Steroids. 3. A New Synthetic Approach to Optically Active Steroids. Total Synthesis of (+)-18-Hydroxyestrone

Plato A. Magriotis; Francis Johnson

doi:10.1021/jo00182a036

Steroids. 3. A New Synthetic Approach to Optically Active Steroids. Total Synthesis of (+)-18-Hydroxyestrone

Plato A. Magriotis
, Francis Johnson

Pharmacological Sciences

Stony Brook University

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

26 Scopus citations

Abstract

A stereospecific synthesis of (+)-18-hydroxyestrone has been accomplished from (S)-malic acid via a chiral β-keto ester intermediate previously used for the synthesis of (+)-PGF_2α The key step involves the coupling of this intermediate with a modified Torgov steroid precursor. The latter reaction is mediated by cupric acetate in aqueous ethanol. Elaboration of the coupled product to the finished steroid follows established methods.

Original language	English
Pages (from-to)	1460-1461
Number of pages	2
Journal	Journal of Organic Chemistry
Volume	49
Issue number	8
DOIs	https://doi.org/10.1021/jo00182a036
State	Published - Nov 1984

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title = "Steroids. 3. A New Synthetic Approach to Optically Active Steroids. Total Synthesis of (+)-18-Hydroxyestrone",

abstract = "A stereospecific synthesis of (+)-18-hydroxyestrone has been accomplished from (S)-malic acid via a chiral β-keto ester intermediate previously used for the synthesis of (+)-PGF2α The key step involves the coupling of this intermediate with a modified Torgov steroid precursor. The latter reaction is mediated by cupric acetate in aqueous ethanol. Elaboration of the coupled product to the finished steroid follows established methods.",

author = "Magriotis, \{Plato A.\} and Francis Johnson",

year = "1984",

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AU - Magriotis, Plato A.

AU - Johnson, Francis

PY - 1984/11

Y1 - 1984/11

N2 - A stereospecific synthesis of (+)-18-hydroxyestrone has been accomplished from (S)-malic acid via a chiral β-keto ester intermediate previously used for the synthesis of (+)-PGF2α The key step involves the coupling of this intermediate with a modified Torgov steroid precursor. The latter reaction is mediated by cupric acetate in aqueous ethanol. Elaboration of the coupled product to the finished steroid follows established methods.

AB - A stereospecific synthesis of (+)-18-hydroxyestrone has been accomplished from (S)-malic acid via a chiral β-keto ester intermediate previously used for the synthesis of (+)-PGF2α The key step involves the coupling of this intermediate with a modified Torgov steroid precursor. The latter reaction is mediated by cupric acetate in aqueous ethanol. Elaboration of the coupled product to the finished steroid follows established methods.

UR - https://www.scopus.com/pages/publications/0021235937

U2 - 10.1021/jo00182a036

DO - 10.1021/jo00182a036

M3 - Article

AN - SCOPUS:0021235937

SN - 0022-3263

VL - 49

SP - 1460

EP - 1461

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 8

ER -

Steroids. 3. A New Synthetic Approach to Optically Active Steroids. Total Synthesis of (+)-18-Hydroxyestrone

Abstract

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