Stereoselective Routes to Polyhydroxylated Cyclohexyl-β-amino Acids

Ishmael B. Masesane; Patrick G. Steel

doi:10.1055/s-2003-38346

LETTER

Stereoselective Routes to Polyhydroxylated Cyclohexyl-β-amino Acids

Ishmael B. Masesane, Patrick G. Steel*
Department of Chemistry, University of Durham, Science Laboratories, South Road, Durham, DH1 3LE, UK
Fax: +44(191)3844737; e-Mail: p.g.steel@durham.ac.uk;

Abstract

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Abstract

The Diels-Alder adduct of ethyl (E)-3-nitroacrylate and furan provides a common and versatile template for the stereocontrolled synthesis of polyhydroxylated cyclohexane β-amino acids derivatives through a strategy involving face selective oxidation and based induced fragmentation of the oxanorbornene skeleton.

Key words

cyclohexyl β-amino acid - nitroacrylate furan cycloadduct - fragmentation - epoxidation - dihydroxylation

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