A highly efficient synthesis of 3-methylcholanthrene

Scientific publication - Journal Article uoadl:2960846 10 Read counter

Unit:
Department of Chemistry
Title:
A highly efficient synthesis of 3-methylcholanthrene
Languages of Item:
English
Abstract:
A five-step synthesis of 3-methylcholanthrene (1) has been achieved starting from 5-methylhomophthalic anhydride and N,N-diethyl-1-naphthamide in 55% over all yield. Treatment of a solution of the preformed lithium enolate of 5-methylhomophthalic anhydride (3) with an equimolar solution of 2-lithio-1-naphthamide (4), followed by acid hydrolysis, provides cleanly the spirobislactone 5 in 80% overall yield. In addition, the synthesis features a unique, highly selective double Friedel-Crafts cyclization of the aryl diacid 2 with PPA to give rise, after acetylation, to keto acetate 6.
Publication year:
1993
Authors:
Thanasis Gimisis
Masato Koreeda
Journal:
The Journal of Organic Chemistry
Publisher:
American Chemical Society (ACS)
Volume:
58
Number:
25
Pages:
7158--7161
Main subject category:
Science
Official URL (Publisher):
DOI:
10.1021/jo00077a045
The digital material of the item is not available.