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Synthesis 2010(22): 3883-3890  
DOI: 10.1055/s-0030-1258263
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Enantiomerically Pure 2,5-Disubstituted 3-Oxygenated Tetrahydrofurans

Carla Álvarez, Manuel Pérez, Andrea Zúñiga, Generosa Gómez*, Yagamare Fall*
Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, 36310 Vigo, Spain
Fax: +34(98)6812262; e-Mail: yagamare@uvigo.es; e-Mail: ggomez@uvigo.es;
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Publication History

Received 26 July 2010
Publication Date:
22 September 2010 (online)

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Abstract

The synthesis of enantiomerically pure 2,5-disubstituted 3-oxygenated tetrahydrofurans has been achieved from cheap and commercially available l-malic acid. This method was used to prepare an advanced intermediate toward CMI-977, a promising candidate for the treatment of chronic asthma.

Key words

furan - tetrahydrofuran - singlet oxygen - butenolide - oxacycles­ - natural products

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