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Journal ArticleDOI

Steroids. Part XXXV. Removal of the 4-methyl groups in 4,4,14α-trimethyl-steroids: conversion of lanosterol into 14α-methylcholest-4-en-3-one

C. W. Shoppee, +3 more
- 01 Jan 1970 - 
- Vol. 10, Iss: 10, pp 1443-1447
TLDR
In this article, the second-order Beckmann cleavage of 3-hydroxyimino-5α-lanostane was used as an intermediate in the conversion of lanosterol into 14α-methylcholest-4-en-3-one.
Abstract
3,4-Seco-5α-lanost-4(30)-en-3-onitrile, obtained by ‘second-order’ Beckmann cleavage of 3-hydroxyimino-5α-lanostane, has been used as an intermediate in the conversion of lanosterol into 14α-methylcholest-4-en-3-one.

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Journal ArticleDOI

Triterpenoids with a Five-Membered a-Ring: Distribution in Nature, Transformations, Synthesis, and Biological Activity

TL;DR: The literature on the distribution in nature, structural variations, isolation, identification, and biosynthesis issues of triterpenoids with a five-membered A-ring was reviewed in this paper.
Journal ArticleDOI

Synthesis, cytotoxic evaluation, and molecular docking studies of the semi-synthetic "triterpenoid-steroid" hybrids.

TL;DR: The molecular docking studies showed that compound 19, which demonstrated most pronounced cytotoxicity against all tested cell lines, fits well the active sites of CDK6 and HER2/neu active sites.
Journal ArticleDOI

Synthesis of obtusifoliol and analogues as CYP51 substrates.

TL;DR: The first chemical synthesis of the final endogenous substrate of this enzyme class, obtusifoliol, is reported in 1.3% yield across ten steps from a commercially available lanosterol mixture, enabling future investigation into CYP51 inhibition to overcome pathogens' azole resistance.