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A Pauson-Khand and ring-expansion approach to the aquariane ring system.

Authors
Type
Published Article
Journal
Organic Letters
1523-7060
Publisher
American Chemical Society
Publication Date
Volume
8
Issue
15
Pages
3195–3198
Identifiers
PMID: 16836364
Source
Medline

Abstract

[Structure: see text] The carbocyclic ring system of the aquariolide diterpenes has been synthesized by two routes involving a diastereoselective Pauson-Khand reaction and subsequent ring expansion. In one route, a tetracyclic enone was elaborated to generate the nine-membered ring by Grob fragmentation. In the second approach, a spirocyclic tricycle underwent a facile anionic oxy-Cope rearrangement to complete the synthesis of the desired ring system.

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