Journal ArticleDOI
Stereocontrolled synthesis of steroid side chain; stereoselective syntheses of cholesterol and 25-hydroxycholesterol
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In this paper, a stereoselective method to introduce side chain onto 17-oxosteroids has been deviced, and using the method cholesterol and 25-hydroxycholesterol are synthesized.About:
This article is published in Tetrahedron Letters.The article was published on 1982-01-01. It has received 11 citations till now. The article focuses on the topics: Side chain.read more
Citations
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Journal ArticleDOI
Cholesterol autoxidation 1981-1986.
TL;DR: The review builds on the detailed 1981 monographic treatment of the topic by the author and covers new items of chemistry, analysis, and metabolism.
Journal ArticleDOI
Organocatalytic Synthesis of Chiral Tetrasubstituted Allenes from Racemic Propargylic Alcohols
TL;DR: It is shown that a highly enantioselective synthesis of tetrasubstituted allenes from racemic propargylic alcohols has been realized by organocatalysis with good efficiency and the process employs quinone methides for axial chirality construction.
Journal ArticleDOI
Rearrangement Reactions, 6. New Functionalized Allenes: Synthesis Using Sigmatropic Rearrangements and Unusual Reactivity
TL;DR: In this article, the synthesis of allenes, which bear a functional group with at least two heteroatoms, by sigmropic rearrangements of appropriate propargyl precursors is summarized.
Journal ArticleDOI
The chemical synthesis of sterols: Latest advances
N. V. Kovganko,S. K. Ananich +1 more
TL;DR: In this paper, a review discusses the results of investigations on the chemical synthesis of sterols during 1981-1996, focusing on the first three decades of the 20th century, and concludes:
References
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Journal ArticleDOI
New stereospecific approach to steroid side chains: conversion of dehydroepiandrosterone to cholesterol, isocholesterol, and their 15.beta.-hydroxy derivatives
Joseph P. Marino,Hiroyuki Abe +1 more
Journal ArticleDOI
Facile, stereoselective synthesis of (24R)-24,25-dihydroxyvitamin D3 using D-glyceric acid as a chiral synthon
TL;DR: In this paper, a facile, stereoselective, and efficient synthesis of (24R)-24,25-dihydroxyvitamin D 3, using D-glyceric acid as a chiral synthon to construct the side chain and ergosterol as a precursor of the secosteroid skeleton, is described.
PatentDOI
Stereocontrolled synthesis of steroidal side chains
William G. Dauben,Todd Brookhart +1 more
TL;DR: In this paper, a method for stereospecifically synthesizing a steroidal side chain is disclosed which provides high yield, and which may be utilized with a variety of steroidal starting materials including unprotected, unsaturated steroidal alcohols.
Journal ArticleDOI
Stereoselective synthesis of (25S)-25-hydroxyvitamin D3 26,23-lactone
TL;DR: Stereoselective synthesis of (25S)-25-hydroxyvitamin D3 26,23-lactone (1w) is described starting from C-22 steroidal aldehyde and (S)-citramalic acid as mentioned in this paper.
Journal ArticleDOI
Simple synthesis of de-AB-cholesta-8(14),22-dien-9-one by highly stereoselective double Michael addition involving alkenylcopper-phosphine complex, vinyl ketone, and 2-methyl-2-cyclopentenone followed by Claisen rearrangement and rhodium-promoted decarbonylation
Related Papers (5)
Stereocontrolled synthesis of steroid side chains via organoboranes. Stereospecific synthesis of 20R- and 20S-25-hydroxycholesterol.
M. Mark Midland,Young C. Kwon +1 more