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Stereoselective Synthesis of Bicyclo[4.2.1]nonanes – a Temporary-Bridge Approach to Cyclooctanoids

✍ Scribed by Antoine Michaut; Sonia Miranda-García; J. Carlos Menéndez; Yoann Coquerel; Jean Rodriguez

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
758 KB
Volume
2008
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

A series of cis‐α,γ‐difunctionalized five‐membered cyclic β‐oxo esters have been chemo‐, regio‐ and diastereoselectively prepared through an efficient domino anionic ring‐cleavage/ring‐reconstitution/alkylation sequence including a 1,3‐shift of the ester group. These unsaturated substrates were successfully engaged in various ring‐closing metatheses to provide a reliable access to functionalized bicyclo[4.2.1]nonanes, precursors of cyclooctanoids following the selective fragmentation of the one‐carbon bridge.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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## Abstract The addition of dichlorocarbene (generated by the interaction of sodium methoxide and ethyl trichloroacetate) to bicyclo[3.2.1]oct‐2‐ene, its 3‐chloro and __exo__‐3,4‐dichloro derivatives gives the __exo__ 1 : 1 adducts in yields of 94, 89 and 48%. By suitable chemical reactions of thes