ENANTIOSELECTIVE ROUTE TO AN AZADIRACHTIN SUBSTRUCTURE

Authors
SCHLESIGER H WINTERFELDT E
Citation
H. Schlesiger et E. Winterfeldt, ENANTIOSELECTIVE ROUTE TO AN AZADIRACHTIN SUBSTRUCTURE, Chirality, 9(5-6), 1997, pp. 454-458
Citations number
16
Categorie Soggetti
Chemistry Medicinal","Pharmacology & Pharmacy
Journal title
Chirality → ACNP
ISSN journal
08990042
Volume
9
Issue
5-6
Year of publication
1997
Pages
454 - 458
Database
ISI
SICI code
0899-0042(1997)9:5-6<454:ERTAAS>2.0.ZU;2-C
Abstract
An enantioselective route to the hydroxyfuran acetal substructure 36 o f azadirachtin is described. The enantiopure key intermediate 29 was o btained in both absolute configurations by a kinetic resolution experi ment, making use of an optical pure cyclopentadiene. After protection of the cyclopentenone double bond a highly diastereoselective reductio n-cyclisation sequence, that may mimic the biogenetic pathway, afforde d the tricyclic framework of the target molecule. (C) 1997 Wiley-Liss, Inc.