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Enantioselective route to an azadirachtin substructure

โœ Scribed by Hartwig Schlesiger; Ekkehard Winterfeldt

Book ID
101294615
Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
45 KB
Volume
9
Category
Article
ISSN
0899-0042

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โœฆ Synopsis

An enantioselective route to the hydroxyfuran acetal substructure 36 of azadirachtin is described. The enantiopure key intermediate 29 was obtained in both absolute configurations by a kinetic resolution experiment, making use of an optical pure cyclopentadiene. After protection of the cyclopentenone double bond a highly diastereoselective reduction-cyclisation sequence, that may mimic the biogenetic pathway, afforded the tricyclic framework of the target molecule.

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