Synthesis and study of a methoxyhydroperoxide-androstenedione derivative; analogue of a potential aromatase intermediate

Philip A. Cole, Cecil H. Robinson

Research output: Contribution to journalArticle

Abstract

A methoxyhydroperoxide analogue (12) to a proposed aromatase intermediate has been synthesized by ozonolysis of methoxyvinyl compound (7) in the presence of methanol; it has been shown not to produce estrone with or without acetylation, but the free hydroperoxide apparently undergoes a facile, stereospecific intramolecular epoxidation.

Original languageEnglish (US)
Pages (from-to)1651-1653
Number of pages3
JournalJournal of the Chemical Society, Chemical Communications
Issue number22
DOIs
StatePublished - 1986

Fingerprint

Acetylation
Aromatase
Epoxidation
Androstenedione
Estrone
Hydrogen Peroxide
Methanol
Derivatives

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Synthesis and study of a methoxyhydroperoxide-androstenedione derivative; analogue of a potential aromatase intermediate. / Cole, Philip A.; Robinson, Cecil H.

In: Journal of the Chemical Society, Chemical Communications, No. 22, 1986, p. 1651-1653.

Research output: Contribution to journalArticle

@article{dd9a721cdc794f66a270523b77036f54,
title = "Synthesis and study of a methoxyhydroperoxide-androstenedione derivative; analogue of a potential aromatase intermediate",
abstract = "A methoxyhydroperoxide analogue (12) to a proposed aromatase intermediate has been synthesized by ozonolysis of methoxyvinyl compound (7) in the presence of methanol; it has been shown not to produce estrone with or without acetylation, but the free hydroperoxide apparently undergoes a facile, stereospecific intramolecular epoxidation.",
author = "Cole, {Philip A.} and Robinson, {Cecil H.}",
year = "1986",
doi = "10.1039/C39860001651",
language = "English (US)",
pages = "1651--1653",
journal = "Chemical Communications",
issn = "1359-7345",
publisher = "Royal Society of Chemistry",
number = "22",

}

TY - JOUR

T1 - Synthesis and study of a methoxyhydroperoxide-androstenedione derivative; analogue of a potential aromatase intermediate

AU - Cole, Philip A.

AU - Robinson, Cecil H.

PY - 1986

Y1 - 1986

N2 - A methoxyhydroperoxide analogue (12) to a proposed aromatase intermediate has been synthesized by ozonolysis of methoxyvinyl compound (7) in the presence of methanol; it has been shown not to produce estrone with or without acetylation, but the free hydroperoxide apparently undergoes a facile, stereospecific intramolecular epoxidation.

AB - A methoxyhydroperoxide analogue (12) to a proposed aromatase intermediate has been synthesized by ozonolysis of methoxyvinyl compound (7) in the presence of methanol; it has been shown not to produce estrone with or without acetylation, but the free hydroperoxide apparently undergoes a facile, stereospecific intramolecular epoxidation.

UR - http://www.scopus.com/inward/record.url?scp=0022921677&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0022921677&partnerID=8YFLogxK

U2 - 10.1039/C39860001651

DO - 10.1039/C39860001651

M3 - Article

AN - SCOPUS:0022921677

SP - 1651

EP - 1653

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 22

ER -