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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 5
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Original Articles

Diverse Reactivities of Corey–Chaykovsky Ylides: Synthesis of 10-Hydroxyaplysin

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Pages 621-626 | Received 09 Aug 2010, Published online: 01 Nov 2011
 

Abstract

The diverse reactivity patterns of the two sulfur ylides 7 and 8 were employed to convert the tricyclic ketone 5 to the isomeric methylene epoxides 9 and 6 respectively. Reduction of 6 followed by bromination furnished the natural product 10-hydroxyaplysin 2.

GRAPHICAL ABSTRACT

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