Synthesis of the Tetronate-Containing Core Structure of the Antibiotic Abyssomicin C

Jean-Philippe Rath; Martin Eipert; Stephan Kinast; Martin E. Maier

doi:10.1055/s-2004-837208

LETTER

Synthesis of the Tetronate-Containing Core Structure of the Antibiotic Abyssomicin C

Jean-Philippe Rath, Martin Eipert, Stephan Kinast, Martin E. Maier*
Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany
Fax: +49(7071)295137; e-Mail: martin.e.maier@uni-tuebingen.de;

Abstract

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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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References

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