Synthesis of enantiomerically pure (3 R,4 R,5 R)-4-hydroxy isoleucine lactone

A short four-step synthesis of (3 R,4 R,5 R)-4-hydroxyisoleucine lactone with total control of stereochemistry is reported, the key intermediate being the didehydroamino acid derivative arising from an aldol dehydration reaction between a glycine anion equivalent and butan-2,3-dione. Graphic

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2001-10, Vol.12 (19), p.2657-2661
Main Authors: Kassem, Tarek, Wehbe, Jonhy, Rolland-Fulcrand, Valérie, Rolland, Marc, Roumestant, Marie-Louise, Martinez, Jean
Format: Article
Language:English
Subjects:
Chemical Sciences
Medicinal Chemistry
Organic chemistry
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Summary:A short four-step synthesis of (3 R,4 R,5 R)-4-hydroxyisoleucine lactone with total control of stereochemistry is reported, the key intermediate being the didehydroamino acid derivative arising from an aldol dehydration reaction between a glycine anion equivalent and butan-2,3-dione. Graphic
ISSN:0957-4166
1362-511X
0957-4166
DOI:10.1016/S0957-4166(01)00465-7