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Synthesis 2005(3): 411-414  
DOI: 10.1055/s-2004-834946
PAPER
© Georg Thieme Verlag Stuttgart · New York

The Methoxyallene Approach to Oxacycles, Part 2: Stereoselective Synthesis of 2,3-Disubstituted Oxepanes

Manuel Pérez, Pilar Canoa, Generosa Gómez, Marta Teijeira, Yagamare Fall*
Departamento de Química Orgánica, Facultad de Química, Universidad de Vigo, 36200, Vigo, Pontevedra, Spain
Fax: +34(98)6812262; e-Mail: yagamare@uvigo.es;
Further Information

Publication History

Received 28 July 2004
Publication Date:
03 December 2004 (online)

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Abstract

2,3-Disubstituted oxepanes 3 and 4 were stereoselectively synthesized from methoxyallene (1) and iodide 2. The trans stereochemistry of diol 3 was established by NMR studies of the bicyclic precursor 10, while the cis stereochemistry of 4 was secured by using the highly diastereoselective reducing agent l-Selectride.

Key words

natural products - methoxyallene - Michael addition - oxepanes - toxins

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