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

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.

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Bibliographic Details
Published inSynthetic communications Vol. 42; no. 5; pp. 621 - 626
Main Authors Roy, Amalesh, Venkateswaran, Ramanathapuram V.
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis Group 01.03.2012
Taylor & Francis
Taylor & Francis Ltd
Subjects
10-hydroxyaplysin
Chemistry
Chemistry, Organic
Corey-Chaykovsky ylides
methylene epoxide
Physical Sciences
Science & Technology
10-hydroxyaplysin
Corey-Chaykovsky ylides
DIMETHYLSULFONIUM METHYLIDE
methylene epoxide
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Summary: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.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2010.528130