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Synlett 2005(10): 1630-1632
DOI: 10.1055/s-2005-869868
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
Weitere Informationen
Received
9 May 2005
Publikationsdatum:
07. Juni 2005 (online)
Publikationsverlauf
Publikationsdatum:
07. Juni 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
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