Ene approach for concurrent control over the chiral centres at C-20 and C-22 of steroid side chains: A highly stereocontrolled synthesis of (20S,22R)-(erythro-)22-hydroxy-23,24-acetylenic steroid side chains

Koichi Mikami; Teck Peng Loh; Takeshi Nakai

doi:10.1039/C39880001430

Ene approach for concurrent control over the chiral centres at C-20 and C-22 of steroid side chains: A highly stereocontrolled synthesis of (20S,22R)-(erythro-)22-hydroxy-23,24-acetylenic steroid side chains

Koichi Mikami, Teck Peng Loh, Takeshi Nakai^*

^*Corresponding author for this work

Tokyo Institute of Technology

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

21 Citations (Scopus)

Abstract

The ene reactions of a (Z)-Δ¹⁷⁽²⁰⁾-steroidal olefin with acetylenic aldehydes in the presence of Me₂AlCl produce (20S,22R)-(erythro)-22-hydroxy-23,24-acetylenic steroid side chains with high diastereoselectivity and diastereofacial selectivity.

Original language	English
Pages (from-to)	1430-1431
Number of pages	2
Journal	Chemical Communications
Issue number	21
DOIs	https://doi.org/10.1039/C39880001430
Publication status	Published - 1988
Externally published	Yes

ASJC Scopus Subject Areas

Molecular Medicine

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title = "Ene approach for concurrent control over the chiral centres at C-20 and C-22 of steroid side chains: A highly stereocontrolled synthesis of (20S,22R)-(erythro-)22-hydroxy-23,24-acetylenic steroid side chains",

abstract = "The ene reactions of a (Z)-Δ17(20)-steroidal olefin with acetylenic aldehydes in the presence of Me2AlCl produce (20S,22R)-(erythro)-22-hydroxy-23,24-acetylenic steroid side chains with high diastereoselectivity and diastereofacial selectivity.",

author = "Koichi Mikami and Loh, {Teck Peng} and Takeshi Nakai",

year = "1988",

doi = "10.1039/C39880001430",

language = "English",

pages = "1430--1431",

journal = "Chemical Communications",

issn = "0022-4936",

publisher = "Royal Society of Chemistry",

number = "21",

}

Ene approach for concurrent control over the chiral centres at C-20 and C-22 of steroid side chains: A highly stereocontrolled synthesis of (20S,22R)-(erythro-)22-hydroxy-23,24-acetylenic steroid side chains. / Mikami, Koichi; Loh, Teck Peng; Nakai, Takeshi.
In: Chemical Communications, No. 21, 1988, p. 1430-1431.

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

TY - JOUR

T1 - Ene approach for concurrent control over the chiral centres at C-20 and C-22 of steroid side chains

T2 - A highly stereocontrolled synthesis of (20S,22R)-(erythro-)22-hydroxy-23,24-acetylenic steroid side chains

AU - Mikami, Koichi

AU - Loh, Teck Peng

AU - Nakai, Takeshi

PY - 1988

Y1 - 1988

N2 - The ene reactions of a (Z)-Δ17(20)-steroidal olefin with acetylenic aldehydes in the presence of Me2AlCl produce (20S,22R)-(erythro)-22-hydroxy-23,24-acetylenic steroid side chains with high diastereoselectivity and diastereofacial selectivity.

AB - The ene reactions of a (Z)-Δ17(20)-steroidal olefin with acetylenic aldehydes in the presence of Me2AlCl produce (20S,22R)-(erythro)-22-hydroxy-23,24-acetylenic steroid side chains with high diastereoselectivity and diastereofacial selectivity.

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U2 - 10.1039/C39880001430

DO - 10.1039/C39880001430

M3 - Article

AN - SCOPUS:0346074945

SN - 0022-4936

SP - 1430

EP - 1431

JO - Chemical Communications

JF - Chemical Communications

IS - 21

ER -

Ene approach for concurrent control over the chiral centres at C-20 and C-22 of steroid side chains: A highly stereocontrolled synthesis of (20S,22R)-(erythro-)22-hydroxy-23,24-acetylenic steroid side chains

Abstract

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