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Enantioselective route to an azadirachtin substructure
Author(s) -
Schlesiger Hartwig,
Winterfeldt Ekkehard
Publication year - 1997
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1997)9:5/6<454::aid-chir10>3.0.co;2-n
Subject(s) - chemistry , enantioselective synthesis , enantiopure drug , kinetic resolution , substructure , stereochemistry , chirality (physics) , acetal , cyclopentenone , azadirachtin , absolute configuration , total synthesis , organic chemistry , catalysis , symmetry breaking , agronomy , chiral symmetry breaking , physics , structural engineering , quantum mechanics , pesticide , nambu–jona lasinio model , engineering , biology
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. Chirality 9:454–458, 1997. © 1997 Wiley‐Liss, Inc.