Synthesis of methylene-bridged polycyclic aromatic hydrocarbons: an efficient, double Friedel-Crafts cyclization approach to 11H-benz[bc]aceanthrylene

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Unit:
Department of Chemistry
Title:
Synthesis of methylene-bridged polycyclic aromatic hydrocarbons: an efficient, double Friedel-Crafts cyclization approach to 11H-benz[bc]aceanthrylene
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% overall 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. 1993 America Chemical Society.
Publication year:
1993
Authors:
Thanasis Gimisis
Jeff W. Kampf
Masato Koreeda
Journal:
The Journal of Organic Chemistry
Publisher:
American Chemical Society (ACS)
Volume:
58
Number:
21
Pages:
5858--5861
Main subject category:
Science
Official URL (Publisher):
DOI:
10.1021/jo00073a058
The digital material of the item is not available.