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Synlett 2005(2): 314-318
DOI: 10.1055/s-2004-837208
DOI: 10.1055/s-2004-837208
LETTER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of the Tetronate-Containing Core Structure of the Antibiotic Abyssomicin C
Further Information
Received
12 November 2004
Publication Date:
17 December 2004 (online)
Publication History
Publication Date:
17 December 2004 (online)
Abstract
The core structure of abyssomicin C (1) containing an oxabicyclooctanone ring and a tetronate was prepared from the addition product of lithium ethyl propiolate and 4-tert-butyldimethylsilyloxycyclohexanone. Tetronate formation via addition of sodium methanolate followed by hydrolysis gave the hydroxy tetronic acid 27. The spiro compound 27 could be cyclized to the tricyclic tetronate 23 by a transannular Mitsunobu lactonization. Alternatively, 27 could be prepared from the cyanohydrin cis-19.
Key words
bicyclics - cyanohydrins - Mitsunobu - ring closure - Wittig reactions
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