The Journal of Organic Chemistry

Furans in synthesis. 5. Furan-terminated cationic cyclizations in the preparation of fused, spirocyclic and bridged ring systems. An application to the synthesis of …

SP Tanis, PM Herrinton

Index: Tanis, Steven P.; Herrinton, Paul M. Journal of Organic Chemistry, 1985 , vol. 50, # 21 p. 3988 - 3996

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Citation Number: 45

Abstract

The title compounds 36-42 and nakafuran 9 (43) were prepared by furan-terminated cationic cyclizations. The cyclization substrates, allylic alcohols 16, 17, 25, 26, 33, and 34, and the derived enone 19 were prepared by CuCN moderated SN2'addition of Grignard reagents derived from 2-(3-furyl)-l-bromoethane (12) and 3-(3-furyl)-l-bromopropane (13) to vinyl epoxides 14 and 22 and epoxy enol ether 21. Treatment of substrate allylic alcohols with a ...

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