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Anodic cyclization reactions: the total synthesis of alliacol a.

Authors
Type
Published Article
Journal
Journal of the American Chemical Society
0002-7863
Publisher
American Chemical Society
Publication Date
Volume
125
Issue
1
Pages
36–37
Identifiers
PMID: 12515499
Source
Medline

Abstract

An anodic cyclization-Friedel Crafts alkylation strategy has been used to rapidly assemble the core ring system of alliacol A and to complete a formal total synthesis of the natural product. The anodic cyclization reaction was used to effect the coupling of a nucleophilic furan ring to the normally nucleophilic carbon of a silyl enol ether. The substrate for this initial cyclization reaction contained all of the carbons needed for completing the total synthesis. The electrolysis proceeded in high yield and could be accomplished with the use of a 6 V lantern battery.

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