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Synthesis 2010(14): 2446-2450  
DOI: 10.1055/s-0029-1218774
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Concise, Enantioselective Synthesis of (+)-Decarestrictine L from Tri-O-acetyl-d-glucal

Andrea Zúñiga, Manuel Pérez, Gonzalo Pazos, Generosa Gómez*, Yagamare Fall*
Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, 36310 Vigo, Spain
Fax: +34(986)812262; e-Mail: yagamare@uvigo.es; e-Mail: ggomez@uvigo.es;
Further Information

Publication History

Received 8 March 2010
Publication Date:
05 May 2010 (online)

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Abstract

We describe a new and efficient approach to the enantio­selective synthesis of (+)-(2R,3S,6R)-decarestrictine L from commercially available tri-O-acetyl-d-glucal, based on a stereoselective Michael addition.

Key words

Michael addition - Wolf-Kishner reaction - Wacker oxidation­

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5

Although d-glucal is commercially available, tri-O-acetyl-d-glucal is much cheaper and can be used for large-scale synthesis.