Steroids and related natural products. Part XLII. 14α-Methyl cholestanes

John C. Knight, John L. Belletire, George Pettit

Research output: Contribution to journalArticle

Abstract

Oxygenation of the 14α-methyl group in 3β-acetoxy-7α- hydroxy-14α-methyl-5α-cholestane has been achieved by reaction with lead tetra-acetate. Cleavage of the resulting 7α,32-epoxide with pyridine hydrochloride in refluxing acetic anhydride gave 3β-acetoxy-14α- acetoxymethyl-5α-cholest-7-ene, while chromium trioxide in acetic acid afforded the lactol derived from 3β-acetoxy-7-oxo-5α-cholestane- 14α-carboxylic acid.

Original languageEnglish (US)
Pages (from-to)2427-2432
Number of pages6
JournalJournal of the Chemical Society C: Organic Chemistry
DOIs
StatePublished - 1967

Fingerprint

Cholestanes
Biological Products
Steroids
Oxygenation
Epoxy Compounds
Carboxylic Acids
Acetic Acid
Acetates

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Steroids and related natural products. Part XLII. 14α-Methyl cholestanes. / Knight, John C.; Belletire, John L.; Pettit, George.

In: Journal of the Chemical Society C: Organic Chemistry, 1967, p. 2427-2432.

Research output: Contribution to journalArticle

@article{a634c3f656634d81890b7d56ff88e5a9,
title = "Steroids and related natural products. Part XLII. 14α-Methyl cholestanes",
abstract = "Oxygenation of the 14α-methyl group in 3β-acetoxy-7α- hydroxy-14α-methyl-5α-cholestane has been achieved by reaction with lead tetra-acetate. Cleavage of the resulting 7α,32-epoxide with pyridine hydrochloride in refluxing acetic anhydride gave 3β-acetoxy-14α- acetoxymethyl-5α-cholest-7-ene, while chromium trioxide in acetic acid afforded the lactol derived from 3β-acetoxy-7-oxo-5α-cholestane- 14α-carboxylic acid.",
author = "Knight, {John C.} and Belletire, {John L.} and George Pettit",
year = "1967",
doi = "10.1039/J39670002427",
language = "English (US)",
pages = "2427--2432",
journal = "Journal of the Chemical Society C: Organic Chemistry",
issn = "0022-4952",
publisher = "Chemical Society",

}

TY - JOUR

T1 - Steroids and related natural products. Part XLII. 14α-Methyl cholestanes

AU - Knight, John C.

AU - Belletire, John L.

AU - Pettit, George

PY - 1967

Y1 - 1967

N2 - Oxygenation of the 14α-methyl group in 3β-acetoxy-7α- hydroxy-14α-methyl-5α-cholestane has been achieved by reaction with lead tetra-acetate. Cleavage of the resulting 7α,32-epoxide with pyridine hydrochloride in refluxing acetic anhydride gave 3β-acetoxy-14α- acetoxymethyl-5α-cholest-7-ene, while chromium trioxide in acetic acid afforded the lactol derived from 3β-acetoxy-7-oxo-5α-cholestane- 14α-carboxylic acid.

AB - Oxygenation of the 14α-methyl group in 3β-acetoxy-7α- hydroxy-14α-methyl-5α-cholestane has been achieved by reaction with lead tetra-acetate. Cleavage of the resulting 7α,32-epoxide with pyridine hydrochloride in refluxing acetic anhydride gave 3β-acetoxy-14α- acetoxymethyl-5α-cholest-7-ene, while chromium trioxide in acetic acid afforded the lactol derived from 3β-acetoxy-7-oxo-5α-cholestane- 14α-carboxylic acid.

UR - http://www.scopus.com/inward/record.url?scp=37049135814&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=37049135814&partnerID=8YFLogxK

U2 - 10.1039/J39670002427

DO - 10.1039/J39670002427

M3 - Article

SP - 2427

EP - 2432

JO - Journal of the Chemical Society C: Organic Chemistry

JF - Journal of the Chemical Society C: Organic Chemistry

SN - 0022-4952

ER -