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Formal Synthesis of 7-Methoxymitosene and Synthesis of its Analog via a Key PtCl2-Catalyzed Cycloisomerization

Author:
Liu, Lianzhu, Wang, Yanzhao, Zhang, Liming
Source:
Organic letters 2012 v.14 no.14 pp. 3736-3739
ISSN:
1523-7052
Subject:
Lewis acids, benzene, bromination, catalytic activity, chemical structure, chemoselectivity, cross-coupling reactions, regioselectivity
Abstract:
A formal synthesis of 7-methoxymitosene is achieved via a key platinum-catalyzed cycloisomerization. The precursor for the Pt catalysis, a fully functionalized benzene intermediate, was prepared via a regioselective electrophilic bromination followed by a chemoselective Sonogashira cross-coupling. It underwent the PtClâ‚‚-catalyzed cycloisomerization smoothly despite its hindered and highly electron-rich nature. Analogs of 7-methoxymitosene can be accessed in an expedient manner by following a similar synthetic sequence.
Agid:
5784101