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OCR for page 350
OCR for page 351
RICHARD BALDWIN TURNER
October 7, 1916-December 22, 1971
BY MARSHALL GATES
RICHARD B. TURNER was born in Minneapolis, Minnesota
on October 7' 1916 to Hubert Michael Turner ant!
Jessie Baldwin Turner, both highly cultured people and edu-
cators. Their son's entire life and career reflected this heri-
tage. Hubert Turner was born in 1882 in HilIsboro, Illinois.
After graduating from the University of TIlinois in 1910, he
stayed on as an assistant instructor for two years while taking
graduate work in mathematics, physics, and electrical engi-
neering. Here he met Jessie Baldwin, a teacher and graduate
of the university in botany. They were married in ~ 9 ~ 2 while
both were members of the faculty of the university.
After an interlude in Minneapolis, where Dick was born,
the family moved to New Haven in lL918 where Hubert Tur-
ner took up an appointment as assistant professor of electri-
cal engineering at the Sheffield Scientific School at Yale. His
entire subsequent career was spent at Yale; he became inter-
nationally known in the field of electrical communication
engineering. He was a member of the American Institute of
Electrical Engineers, the International Union of Scientific
Radio Telegraphy, the Franklin Institute, the Institute of
Raclio Engineers, the American Standards Association, and
the American Association for the Advancement of Science.
351
OCR for page 352
352
BIOGRAPHICAL MEMOIRS
He retired from Yale in 1952 anct cTiect of a heart attack while
living at the Yale Faculty Club in 1965.
Dick's mother, Jessie Baldwin Turner, was born in Deer
Park, Illinois. She maintained her interest in botany in New
Haven, where she was a member of the Fern Society ant! had
a collection of over one hunctrect varieties of ferns. Both
parents collected rocks, shells, and stamps ant! were evict bird
watchers. They were widely react and well informed, of high
principles, interested in both worIct ant! local affairs, and
maintained a home in which intellectual values were fostered.
Dick's only sibling, Elizabeth, stied at age nine, and he was
raised as an only chitct from then on. He spent all his chilcI-
hood in New Haven, strongly influenced by his parents and
the college community. He attencled Susan Sheridan Junior
High School and New Haven High School, graduating in
1933. He was a bright ant! inquisitive chilcI, excelling in
mathematics, physics, and chemistry. Both parents supple-
mentect and enriched his formal education by tutoring him at
home.
Turner was also a talentec! musician ant! cluring these
years playecl the piano, clarinet, and trombone. This talent
for and love of music was to remain with him all his life; he
particularly enjoyed Dixieland jazz and was aclept in this style
with the clarinet. While at Harvard he played in the college
banct. Like most boys of his age, he was keenly interested in
athletics, and he also enjoyed sailing ant! woodworking. In
later years he found time to combine the last two avocations,
building a sailboat that he ant! his family greatly enjoyed!
using. He was also an evict reacler, particularly in history, and
was ectitor-in-chief of his school newspaper, The Sentinel, his
. . -
~un~or ant senior years.
In ~ 934 Turner entered Harvard, graduating in ~ 938. He
remained at Harvarc! for graduate studies, first uncler Wil-
liam F. Ross, then with Louis F. Fieser, uncler whom he com-
OCR for page 353
RICHARD BALDWIN TURNER
353
pleted his Ph.D. in 1942. He remained at Harvarc! for
another year working under a National Defense Research
Committee contract, then went to the Mayo Clinic in 1943 to
work with the group assembled by E. C. Kendall to examine
the chemistry of the adrenocorticosteroicis. After two years at
the Mayo Clinic, Turner in 1945 joined a synthetic group at
MIT carrying on a wartime project on the synthesis of antima-
larials under the ctirection of Arthur C. Cope. He remained
with this group until 1948, when he returned to Harvard as
a research fellow of the American Cancer Society, for the first
time working alone or with one or two technicians on prob-
lems of his own inception. He remained there until the fall of
195 I, when he took a position as assistant professor of chem-
istry at Rice University, rising through the academic ranks to
associate professor (1953) and professor (1956~. He re-
mainect at Rice for the rest of his career.
In 1952 Turner married Halina Deschko, a native of the
Ukraine who had come to this country after World War IT.
She had graduated from Mt. Holyoke and the Simmons Col-
lege School of Social Work. They tract three children:
Richard, Jr., Tamara, and William. Richard, fir., is an archi-
tect and his younger brother, William, is also entering this
fielct; Tamara's professional interests lie in anthropology.
Turner was a devoted husband! ant! father and spent much
time with his family in spite of the heavy demands of his
professional career.
Turner was an unusually able teacher and lecturer. His
presentations, both in the classroom anc! at symposia anc!
meetings, were sharp, incisive, rigorous, and polished, and he
was invited to present his work widely both here ant! abroad.
THE SCIENTIFIC WORK OF R. B. TURNER
Aside from the work he carrier! out for his Ph.D., Richard
Turner's first significant contribution to chemistry came
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354
BIOGRAPHICAL MEMOIRS
from the two years he spent with Kendall's group at the Mayo
Clinic. A series of six papers on the general subject of steroids
derived from bile acids appeared in the period from 1946 to
1952. Using ~9'~ choleric acid as a raw material, efficient
methods were developed for the preparation of the impor-
tant ~ I-ketocholanic acid and a number of its close relatives
ant! the subsequent degradation of ~ I-ketocholanic acid to
Il-ketoetiocholanic acid! by removal of the bile acid sicle
chain. This work was crucial for the preparation of the first
partially synthetic samples of Kendall's compound A for clini-
cal trials. During the course of this work, stereochemical as-
signments were macle to twenty-five bile acid derivatives
substituted in ring C.
Turner's interest in steroids ant! relates! compounds en-
clured in somewhat modified form throughout his career. He
was the first to synthesize C~4 labeled cholestenone and testos-
terone ~ ~ 947), and sporadic publications on a variety of prob-
lems related to steroids appeared from then until 1960.
During the period from 1954 to 195S, Turner ant! his co-
workers carried out structural studies on the carcliotonic ste-
roicI ouabagenin, derived from the glycoside ouabain long
user! as an arrow poison by the East African Somalis. They
were able to locate the remaining uncertain hyciroxyl group
at C ~ ~ and were able to correlate ouabagenin and strephan-
thidine, another carcliotonic aglycone, by conversion of both
to a common derivative still retaining the hydroxyl group at
CI4 and the butanolide ring.
A general interest in the structure and synthesis of natural
substances, of which the above work in the steroid field was
one manifestation, continued to occupy Turner throughout
most of his career. Determination of the structure and com-
pletion of a synthesis of cassaic acid ant! a synthesis of phyllo-
cIaden were published in the perioc! from 1959 to 1966, and
he and his coworkers had begun a synthetic approach to the
OCR for page 355
RICHARD BALDWIN TURNER
355
diterpenoid alkaloids at about this time. At the time of his
cleath, Turner and his coworkers were at work on a synthesis
of marasmic acid! and hac! completed construction of the
carbon skeleton in its correct stereochemical form. Various
syntheses of intermediates used in the extensive antimalarial
program carried out (luring the later stages of WorIcl War 11[
comprise the work Turner carried out while in the group
heaciecl by Arthur C. Cope in the period from 1945 to 1948.
Synthetic work in the naphthoquinone field with Louis F.
Fieser formed the subject of his cloctoral dissertation as well;
these results were publisher! in 1947.
In a penetrating and important early paper, Turner, in
collaboration with Dorothy VoitIe, established the structure
of ~~-~-acetyI-2-methy~cyclohexene as the s-cis conformer;
this was done by a study of its uv absorption ant! that of a
number of more rigid! a,,B-unsaturated ketones and provider!
an explanation of the lowered extinction coefficients in such
substances.
Turner's bibliography contains contributions on a wide
variety of subjects (synthesis, structures of natural products,
use of radioactive carbon in labeling important hormones,
confirmational analysis, instrumental methods as probes of
structure, stereochemistry, ant! such diverse biochemical sub-
jects as the mechanism of uptake of radioactive iodine by
thyroid tissue and the biochemistry of alclosterone), but by
far the most important contribution he and his colleagues
maple was their use of heats of hydrogenation as a too! to
study a variety of problems having to do with the comparative
stabilities of a wide variety of olefins, estimates of strain ener-
gies ant! conjugative interactions, confirmational problems,
and others. This work brought order based on quantitative
results to a large and important area of organic chemistry
that theretofore had been characterized by conjecture, hy-
pothesis, and speculation.
.
OCR for page 356
356
BIOGRAPHICAL MEMOIRS
It is perhaps inappropriate to review this work in detail
here, but the following important results and conclusions
arose directly from it:
· The question of homoallylic resonance in such sub-
stances as norbornadiene, barrelene, and cis, cis, cis-11,4,7-
cyclononatriene was resolved once and for all. They are de-
void of such resonance.
· The relative stabilities of various double-bond isomers
of cholestene were established on a quantitative basis (~2 is
the most stable).
· The relative stabilities of cis and bans
.
Isomers of cy-
clooctene, cyclononene, and cycloclecene were quantitatively
cleterminect. In any given pair, the cis isomer is more stable,
cas-cyclodecene having the lowest enthalpy of hydrogenation
of any alkene examined.
· Reliable values for the stabilization energies of a
number of theoretically important cyclic polyenes were estab-
lished. Among those studied were cyclooctatetrene; I,3,5-
cyclooctatriene; azulene; heptafuIvene; heptafuIvalene and
its dihydro derivative, tropone
pleiaclylene.
tropylium ion; and ace-
· The relative stabilities of exo and undo olefins in five-,
six-, and seven-membered ring systems were cletermine~l. In
all cases, the enclo isomer is the more stable. There tract been
claims, albeit somewhat ambiguous, that couIct have been
interpreted as indicating a greater stability for the exo isomer
in five-membered rings.
· The order of stability for substituted olefins was estab-
lished unambiguously. This work also showed the impor-
tance of planarity for olefin stability; cis-di-t-butylethylene
has the highest enthalpy of hydrogenation of any simple
olefin examined, nearly 10 kcal/mole higher than its bans
isomer.
OCR for page 357
RICHARD BALDWIN TURNER
357
· The essential correctness of a single most stable confor-
mation for cyclociecane, suggested by Dunitz, was established
by the demonstration of the necessity for a transoid confor-
mation in I, I,4,4-tetramethy~cyclodecen-7.
· The well-known stabilizing effect of alky! groups on
carbon-carbon double-bonds was shown to be independent
of the nature of the alkyd group and therefore not readily
accounted for on steric grounds.
· The strain energies of a number of theoretically in-
. . ~
teresting small ring compounds were determined. I,3-
Dimethy~bicyclof I. I.0] butane has the remarkably high value
of 67 kcaVmole.
· The conjugative stabilization in 2-methyI-l,3,5-hexa-
triene was shown not to be the result of strengthening of
sp2-sp2 bonds relative to sp3-sp2 bonds, but to be consistent
with the resonance hypothesis. By inference, this finding
should also apply to I,3-butadiene ant! I,3,5-hexatriene and
similar substances.
· The triple-bone! strain in cyclic alkynes was cletermined.
It is large in cyclooctyne, about 2.9 kcaVmole in cyclononyne
and negligible in ten- ant! tweIve-membered rings.
· Reliable quantitative evidence on strain and conjugative
interactions in such substances as the cyclohexaclienes and
the cycloheptaclienes, as well as in the cyclooctatrienes, was
provident. These data will have to be taken into account in any
discussion of such meclium-size ring systems.
· Quantitative evidence for transannular interactions in
medium-size rings, both saturated and unsaturated, was ac-
cumulated.
In this large and important field Turner perceived the
need for reliable quantitative data, selected the substrates to
be examined with a keen eye for the significance of the f~nd-
ings, provided the methodology for obtaining them, mea-
OCR for page 358
358
BIOGRAPHICAL MEMOIRS
sured the quantities with precision, and interpreted the re-
sults with rigor and sophistication.
The importance of this work as a whole attracted much
attention, and led to fruitful collaboration with other well-
known chemists both here and abroad. The most extensive
such collaboration was between Turner and William von E.
Doering. They and their collaborators published five joint
papers.
Finally, it is remarkable that nearly 20 percent of Turner's
papers were published under his name alone. He was a gifted
experimentalist and enjoyed laboratory work. He continued
to carry on experimentation with his own hands right up to
the time of his death.
OCR for page 359
RICHARD BALDWIN TURNER
BIBLIOGRAPHY
1941
359
With W. F. Ross. Hemo-globin linkage of hemoglobin. II. Analysis
of the CO product. The pancreatic digestions of several forms
of hemoglobin. I. Biol. Chem., 139:603-10.
1946
With V. R. Mattox, L. L. Engel, B. F. McKenzie, and E. C. Kendall.
Steroids derived from bile acids. III. Derivatives of /\9 ii cho-
lenic acid with substituents at C3 and Cot. }. Biol. Chem.,
162:571-84.
With V. R. Mattox, L. L. Engel, B. F. McKenzie, W. F. McGuckin,
and E. C. Kendall. Steroids derived from bile acids. IV.
3,9-Epoxy-/\ choleric acid and closely related compounds. I.
Biol. Chem., 164: 569-96.
With V. R. Mattox, L. L. Engel, B. F. McKenzie, and E. C. Kendall.
Steroids derived from bile acids. V. Introduction of oxygen at
Cal. I. Biol. Chem., 166:34~65.
With A. C. Cope. ~x(Dialkylaminomethyl)-2-phenyl-4-quinoline-
methanols with 8-amino or hydroxy substituents. I. Am. Chem.
Soc., 68:221~19.
With }. Mills and A. C. Cope. c~(Dialkylaminomethyl)-8-amino (or
hydroxy)-4-quino-linemethanols. I. Am. Chem. Soc., 68:
222() 24.
1947
Radioactive cholestenone. I. Am. Chem. Soc., 69:72~27.
Radioactive testosterone. Science, 106:248.
With L. F. Fieser. Addition of mercapto derivatives to 2-methyl-
1,4-naphthoquinone. I. Am. Chem. Soc., 69:233~38.
With L. F. Fieser. Naphthoquinone acids and ketols. I. Am. Chem.
Soc., 69:2338-41.
1948
Structure and synthesis of cardiac genies. Chem. Rev., 43:1-42.
With V. R. Mattox, B. F. McKenzie, L. L. Engel, and E. C. Kendall.
Steroids derived from bile acid. VII. Probable stereochemical
configuration of some derivatives of the bile acids. I. Biol.
Chem., 173:283-94.
OCR for page 360
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OCR for page 364
OCR for page 365
360
BIOGRAPHICAL MEMOIRS
1949
With A. C. Cope, H. R. Nace, W. R. Hatchard, W. H. Jones, and
M. A. Stahmann. Synthesis of 6-methoxy-8-amino-quinoline de-
rivatives. Ethylenimine rearrangements in attachment of
monoalkylamino-alkyl side chains. I. Am. Chem. Soc., 7 1:
554 61.
1950
Steroids labeled with isotopic carbon: Cholestenone and testos-
terone. I. Am. Chem. Soc., 72:57~85.
With D. M. Voitle. Preparation of D~-cysteine hydrochloride. I. Am.
Chem. Soc., 72:628-29.
Stereochemistry of the peracid oxidation of ketones. l. Am. Chem.
Soc., 72:878-82.
With D. M. Voitle. Reaction of 1-acetyl-2-methylcyclohexene with
cyclohexanone. T. Am. Chem. Soc., 72:416~68.
1951
With D. M. Voitle. The structure of 1-acetyl-2-methylcyclohexene;
Spectral characteristics of s-cas-
RICHARD BALDWIN TURNER
1953
361
With R. B. Woodward. Chemistry of the cinchona alkaloids. In: The
Alkaloids Chemistry and Physiology, vol. 3, p. 1. New York: Aca-
demic Press.
Stereospecificity in the rearrangement of 17-hydroxy-20-oxo ste-
roids. I. Am. Chem. Soc., 75:348~88.
With R. P. A. Sneeden. Ouabagenin. I. The relationship between
ouabagenin monoacetonide and anhydroouabagenin. I. Am.
Chem. Soc., 75:3510-13.
Acylation of 17-hydroxy-20-oxo-steroids. I. Am. Chem. Soc., 75:
3489-92.
With H. R. Nace. Dipole moments and conformations of
androstane-3,17-dione and of etiocholane-3,17-dione. I. Am.
Chem. Soc., 75:4063-66.
Infrared absorption of some steroid digitonides. I. Am. Chem.
Soc., 75:4362-63.
Molecular rotation differences for 17-hydroxy-20-keto steroids. I.
Am. Chem. Soc., 75:3604-5.
1954
With R. P. A. Sneeden. Structure of ouabagenin. Chem. Ind.,
1954: 1235-36.
With H. I. Nachimson, R. H. Benson, I. I. Szafir, H. C. Allen, Jr.,
and R. V. Talmage. Comparative study of effects of phenothia-
zine and iodine on thyroid uptake of iodine. Proc. Soc. Exp.
Biol. Med., 87:157-62.
Pyrolysis of the Windaus acid. I. Am. Chem. Soc., 76: 1390.
1955
With R. P. A. Sneeden. Ouabagenin. II. The hydroxyl groups of
the A/B ring system. {. Am. Chem. Soc., 77:130-34.
With R. P. A. Sneeden. Catalytic dehydrogenation of primary and
secondary alcohols with platinum and oxygen: Selective dehy-
drogenation in the steroid series. I. Am. Chem. Soc., 77: 190-91.
With R. Anliker. Stereochemistry of the epimeric 17c`-methyl-D-
homo-testosterones. Helv. Chim. Acta, 38:411-20.
1956
With R. V. Talmage, R. H. Benson, I. I. Szafir, and H. C. Allen.
Excess iodide as the primary cause of the inhibition of thyroid
362
BIOGRAPHICAL MEMOIRS
uptake of radioiodine produced by phenothiazine N. F. (green).
I. Am. Vet. Med. Assoc., 128: 150~51.
With I. A. Meschino. Location of the sixth hydroxyl group in oua-
bagenin. I. Am. Chem. Soc., 78:5130-31.
With D. E. Nettleton, Jr., and R. Ferebee. Synthetic routes to
3,6-dimethoxyphenanthrene. I. Am. Chem. Soc., 78:5923-27.
1957
With R. L. Anliker, A. S. Lindsey, and D. E. Nettleton, Jr. A syn-
thetic approach to polycyclic hydroaromatic systems related to
the 19-nonsteroids. I. Am. Chem. Soc., 79:220-26.
With R. H. Garner. Stability relation of 1-methylcyclopentene and
methylenecyclopentane. I. Am. Chem. Soc., 79:253.
With M. Perelman and K. T. Park, fir. Tracer studies in rearrange-
ments of 17-hydroxy-20-oxosteroids and observations on the
reaction of compound ~ monoacetate with Al isopropoxide. J.
Am. Chem. Soc., 79:1108-14.
With W. R. Meador and R. E. Winkler. Heats of hydrogenation. I.
Apparatus and the heats of hydrogenation of bicyclo[2.2.1]hep-
tadiene bicyclof2.2.2joctane and bicyclo[2.2.2]octadiene. i. Am.
Chem. Soc., 79:4116-21.
With W. R. Meador and R. E. Winkler. Heats of hydrogenation. II.
Heats of hydrogenation and the acid catalyzed isomerization of
unsaturated steroids. I. Am. Chem. Soc., 79:4122-27.
With W. R. Meador, W. v. E. Doering, L. H. Knox, I. R. Mayer, and
D. W. Wiley. Heats of hydrogenation. III. Hydrogenation of
cycloocta tetraene and of seven-membered nonbenzenoid aro-
matic compounds. I. Am. Chem. Soc., 79:4127-33.
With W. R. Meador. Heats of hydrogenation. IV. Hydrogenation
of cats and tra7's-cycloolefins. J. Am. Chem. Soc., 79:4133-36.
, ,~
1958
With R. H. Garner. Heats of hydrogenation. V. Relative stabilities
in exocyclic endocyclic olefin pairs. J. Am. Chem. Soc.,
80: 1424-30.
With D. E. Nettleton, fir., and M. Perelman. Heats of hydrogena-
tion. VI. Substituted ethylene. I. Am. Chem. Soc., 80: 1430-33.
With J. A. Meschino. Ouabagenin. III. Assignment of the sixth
hydroxyl group and a structural correlation with strophanthi-
din. J. Am. Chem. Soc., 80:4862-65.
RICHARD BALDWIN TURNER
1959
363
Stabilization and strain energies from heats of hydrogenation. Ke-
kule Symposium on Theoretical Organic Chemistry, London,
1958. In: Theoretical Organic Chemistry, p. 67. London: Butter-
worths Scientific Publications.
With E. G. Herzog, K. B. Morin, and A. Riebel. Structure of cassaic
acid. Tetrahedron Lett., 1959, 2: 7-10.
Thermal evidence for hyperconjugation. Tetrahedron, 5:127-34.
1960
With P. E. Shawl Total synthesis of a degradation product of phyl-
locladene. Tetrahedron Lett., 18:2~27.
With H. R. Nace. Dipole moments of androstan- 17-one, testan- 11-
one, and testane-11,17-dione. I. Org. Chem., 25:1403-4.
With H. Prinzbach and W. v. E. Doering. Heats of hydrogenation.
VII. Cycloheptatrienylium~tropylium) ion. J. Am. Chem. Soc.,
82:3451-54.
With R. H. Benson. Acetyl group determination using acetic an-
hydride Ci4. Anal. Chem., 32:1464-65.
1961
With R. E. Lee and E. G. Hildenbrand. Trans-decalin-2,9-
dicarboxylic acid and related derivatives. I. Org. Chem.,
26:4800~803.
With K. H. Ganshirt. Total synthesis of phyllocladene. Tetra-
hedron Lett., 1961, 231-33.
1964
With P. Goebel, l. Sicher, and M. Svoboda. Conformation of un-
saturated cyclodecane derivatives. Enthalpy of hydrogenation
of alkylcyclodecenes and -cyclodecynes. Proc. Chem. Soc. Lon-
don (July):237-38.
With W. R. Roth, W. B. Bang, P. Goebel, R. L. Sass, and A. P. Yue.
Question of homoconjugation in As, As, cas-1,4,7-cyclonona-
triene. J. Am. Chem. Soc., 86~15~:3178-79.
Heat of hydrogenation of bicyclof2.2.2]octa-2,5,7-triene. I. Am.
Chem. Soc., 86~17~:3586-87.
With P. Grafen. 1-Cyano-5-methoxy-2-tetralone. Tetrahedron
Lett., 52:3935-37.
364
BIOGRAPHICAL MEMOIRS
1965
With P. Goebel, W. v. E. Doering, and I. F. Coburn. Strain in
1,3-dimethylbicyclof 1,1,0]butane. Tetrahedron Lett., 1965,
997-1002.
1966
With I. Sicher, M. Svoboda, I. Zavada, and P. Goebel. Stereo-
chemical studies. Part 36. An approach to conformational analy-
sis of medium ring compounds, unsaturated 10-membered ring
derivatives. Tetrahedron, 22:659-71.
With O. Buchardt, E. Herzog, R. B. Morin, A. Riekl, and I. M.
Sanders. Structure and total synthesis of cassaic acid. I. Am.
Chem. Soc., 88:1766-75.
With K. W. Ganshirt, P. E. Shaw, and I. D. Tauter. Total synthesis
of phyllocladene. J. Am. Chem. Soc., 88: 1776-85.
With G. D. Diana, G. E. Fodor, K. Gebert, D. L. Simmons, A. S. Rao
O. Roos, and W. Wirth. Synthetic intermediates related to
diterpene alkaloid. I. Am. Chem. Soc., 88:1786-92.
1968
With I. Sicher, M. Svoboda, and B. I. Mallon. Stereochemical stud-
ies. 47. Conformational analysis of many-membered ring com-
pounds. Cyclododecenes. }. Chem. Soc., 1968B:441~7.
With R. D. Stipanovic. Cyclohexenone-4-acetic acid derivatives
from the addition of diazoacetic ester to beta, gamma unsatu-
rated ketals. J. Org. Chem., 33:3261-63.
With P. Goebel, B. I. Mallon, W. v. E. Doering, I. F. Coburn, and
M. Pomerant. Heats of hydrogenation. VIII. Compounds with
3- and 4-membered rings. I. Am. Chem. Soc., 90:4315-22.
With R. B. Miller and I. L. Lin. Stereochemical investigations of
methyl epimerization in derivatives of 1-methyl-trans-decalin.
J. Am. Chem. Soc., 90:612~30.
With P. Grafen, H. I. Kabbe, O. Roos, G. D. Diana, and T. T. Li.
Synthetic approaches to diterpene alkaloids. I. Am. Chem. Soc.,
90:6131-35.
With P. M. Lesko. Strain energy in bicyclof3,3,1]non-1-ene. J. Am.
Chem. Soc., 90:688~89.
RICHARD BALDWIN TURNER
365
1970
With M. Tichy. Heats of hydrogenation of c~s-2-methylhexatriene
and trans-2-methylhexatriene resonance or sigma bond energy.
Proc. Natl. Acad. Sci. USA, 67~4~:12A.
With L. P. Cawley, S. C. Sommers, and R. Horton. Biochemistry
and physiology of aldosterone. Am. I. Clin. Pathol., 54:311-13.
Chemical properties of aldosterone. Am. I. Clin. Pathol.,
54 28~96.
1971
With A. Meyer. Interesting synthesis of 3-methoxy-2,6-dimethyl-
phenethyl alcohol. Tetrahedron, 27:2609-15.
With V. Boekelheide and W. S. Lindsay. Heats of hydrogenation.
Acepleiadylene. Tetrahedron, 27(151:3341~4.
1973
With P. Goebel, B. I. Mallon, and A. D. Barrett. Heats of hydro-
genation. IX. Cyclic acetylenes and some miscellaneous olefins.
I. Am. Chem. Soc., 95:790-92.
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