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Synlett 2005(10): 1630-1632  
DOI: 10.1055/s-2005-869868
LETTER
© Georg Thieme Verlag Stuttgart · New York

Studies towards the Synthesis of Rapamycin: Regiocontrol in the Addition of Carbanions to Enantiomerically Pure Epoxides and the Formation of a Highly Substituted Tetrahydrofuran

Kyungsoo Oha, David Cheshireb, Philip J. Parsons*a
a Department of Chemistry, School of Life Sciences, University of Sussex, Falmer, Brighton, East Sussex BN1 9QJ, UK
e-Mail: P.J.Parsons@sussex.ac.uk;
b Department of Medicinal Chemistry, AstraZeneca Charnwood Laboratories, Bakewell Road, Loughborough, Leicestershire LE11 5RH, UK
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Publication History

Received 9 May 2005
Publication Date:
07 June 2005 (online)

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Abstract

Reaction of trimethylaluminium, dimethyllithium cuprate and lithium tetramethylaluminate with the homochiral epoxide 8 has been studied. Intermolecular epoxide ring-opening was observed with dimethyllithium cuprate and lithium tetramethylaluminate, but acetal ring-opening followed by intramolecular epoxide ring-opening was observed with trimethylaluminium.

Key words

rapamycin - epoxide-opening - substituted tetrahydrofuran - trimethylaluminium - lithium tetramethylaluminate