Steroid conformations in solid and solution: Stereoselective synthesis of (20S)- and (20R)-[20-methyl-labelled]-20-methylpregn-5-ene-3β,17α,20- triol

Yoshio Osawa; Takuo Makino; Kenyu Shibata; Charles M. Weeks; William L. Duax

doi:10.1039/C39760000991

Steroid conformations in solid and solution: Stereoselective synthesis of (20S)- and (20R)-[20-methyl-labelled]-20-methylpregn-5-ene-3β,17α,20- triol

Yoshio Osawa
, Takuo Makino
, Kenyu Shibata
, Charles M. Weeks
, William L. Duax

Department of Structural Biology

Hauptman-Woodward Medical Research Institute, Inc.

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

Addition of isotopically labelled methylmagnesium bromide followed by reduction with lithium aluminium hydride of 17α-hydroxypregnenolone 3-acetate and 16α,17α-epoxypregnenolone acetate gave, respectively, (20S)- and (20R)-[20-¹³CH₃]-,[20-C³H ₃]-, and [20-C²H₃]-20-methylpregn-5-ene- 3β,17α,20-triol (99% for S, 93% for R) owing to conformational localization of the 20-carbonyl group to positions of opposite chirality caused by neighbouring substitution.

Original language	English
Pages (from-to)	991-993
Number of pages	3
Journal	Journal of the Chemical Society D: Chemical Communications
Issue number	23
DOIs	https://doi.org/10.1039/C39760000991
State	Published - 1976

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title = "Steroid conformations in solid and solution: Stereoselective synthesis of (20S)- and (20R)-[20-methyl-labelled]-20-methylpregn-5-ene-3β,17α,20- triol",

abstract = "Addition of isotopically labelled methylmagnesium bromide followed by reduction with lithium aluminium hydride of 17α-hydroxypregnenolone 3-acetate and 16α,17α-epoxypregnenolone acetate gave, respectively, (20S)- and (20R)-[20-13CH3]-,[20-C3H 3]-, and [20-C2H3]-20-methylpregn-5-ene- 3β,17α,20-triol (99\% for S, 93\% for R) owing to conformational localization of the 20-carbonyl group to positions of opposite chirality caused by neighbouring substitution.",

author = "Yoshio Osawa and Takuo Makino and Kenyu Shibata and Weeks, \{Charles M.\} and Duax, \{William L.\}",

year = "1976",

doi = "10.1039/C39760000991",

language = "English",

pages = "991--993",

journal = "Journal of the Chemical Society D: Chemical Communications",

issn = "0022-4936",

publisher = "Chemical Society",

number = "23",

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TY - JOUR

T1 - Steroid conformations in solid and solution

T2 - Stereoselective synthesis of (20S)- and (20R)-[20-methyl-labelled]-20-methylpregn-5-ene-3β,17α,20- triol

AU - Osawa, Yoshio

AU - Makino, Takuo

AU - Shibata, Kenyu

AU - Weeks, Charles M.

AU - Duax, William L.

PY - 1976

Y1 - 1976

N2 - Addition of isotopically labelled methylmagnesium bromide followed by reduction with lithium aluminium hydride of 17α-hydroxypregnenolone 3-acetate and 16α,17α-epoxypregnenolone acetate gave, respectively, (20S)- and (20R)-[20-13CH3]-,[20-C3H 3]-, and [20-C2H3]-20-methylpregn-5-ene- 3β,17α,20-triol (99% for S, 93% for R) owing to conformational localization of the 20-carbonyl group to positions of opposite chirality caused by neighbouring substitution.

AB - Addition of isotopically labelled methylmagnesium bromide followed by reduction with lithium aluminium hydride of 17α-hydroxypregnenolone 3-acetate and 16α,17α-epoxypregnenolone acetate gave, respectively, (20S)- and (20R)-[20-13CH3]-,[20-C3H 3]-, and [20-C2H3]-20-methylpregn-5-ene- 3β,17α,20-triol (99% for S, 93% for R) owing to conformational localization of the 20-carbonyl group to positions of opposite chirality caused by neighbouring substitution.

UR - https://www.scopus.com/pages/publications/37049101765

U2 - 10.1039/C39760000991

DO - 10.1039/C39760000991

M3 - Article

AN - SCOPUS:37049101765

SN - 0022-4936

SP - 991

EP - 993

JO - Journal of the Chemical Society D: Chemical Communications

JF - Journal of the Chemical Society D: Chemical Communications

IS - 23

ER -

Steroid conformations in solid and solution: Stereoselective synthesis of (20S)- and (20R)-[20-methyl-labelled]-20-methylpregn-5-ene-3β,17α,20- triol

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