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Solution and Solid-Phase Synthesis of Functionalized 3-Arylbenzofurans by a Novel Cyclofragmentation – Release Pathway

✍ Scribed by K. C. Nicolaou; Scott A. Snyder; Antony Bigot; Jeffrey A. Pfefferkorn

Publisher
John Wiley and Sons
Year
2000
Tongue
English
Weight
134 KB
Volume
112
Category
Article
ISSN
0044-8249

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✦ Synopsis

The 3-arylbenzofuran nucleus is a central component of a diverse class of heterocyclic natural and synthetic products that possess a broad range of biological activities. [1] During the course of recent synthetic investigations we discovered a novel reaction cascade leading to 3-phenylbenzofuran (1, Scheme 1), the core structure of the 3-arylbenzofuran class. This serendipitous observation occurred as a result of attempts to convert epoxide 2 (see Scheme 2 for its preparation) into 3 by deprotonation of the methylene group adjacent to the sulfone followed by selective opening of the epoxide ring. Surprisingly, rather than providing the desired system 3, the only product observed was benzofuran 1. The proposed mechanism for this transformation, a novel cyclofragmentation pathway, is outlined in Scheme 1, in which after the initial generation of the alkoxide intermediate 4 from a 5-exo-trig cyclization, collapse to 1 occurs by the concomitant expulsion O S Ph

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