TY - JOUR
T1 - Stereoconvergent route to chiral cyclohexenone building blocks
T2 - Formal synthesis of (-)-dysidiolide
AU - Moustafa, Gamal A.I.
AU - Kamada, Yasumasa
AU - Tanaka, Tetsuaki
AU - Yoshimitsu, Takehiko
N1 - Copyright:
Copyright 2013 Elsevier B.V., All rights reserved.
PY - 2012/11/21
Y1 - 2012/11/21
N2 - A stereoconvergent access to chiral carbocyclic building blocks is reported. 6-(3′-Hydroxy-4′-methylpent-4′-enyl)-3-methoxy cyclohex-2-enone (1) that consists of four stereoisomers, i.e., racemic ca. 1:1 diastereomers, is converted to enantiomerically pure carbocycles through a combination of regioselective catalytic asymmetric reduction and alkylative remote stereoinduction. The present stereoconvergent strategy has allowed the formal synthesis of bioactive (-)-dysidiolide.
AB - A stereoconvergent access to chiral carbocyclic building blocks is reported. 6-(3′-Hydroxy-4′-methylpent-4′-enyl)-3-methoxy cyclohex-2-enone (1) that consists of four stereoisomers, i.e., racemic ca. 1:1 diastereomers, is converted to enantiomerically pure carbocycles through a combination of regioselective catalytic asymmetric reduction and alkylative remote stereoinduction. The present stereoconvergent strategy has allowed the formal synthesis of bioactive (-)-dysidiolide.
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U2 - 10.1039/c2ob26532j
DO - 10.1039/c2ob26532j
M3 - Article
C2 - 23042006
AN - SCOPUS:84867514330
VL - 10
SP - 8609
EP - 8615
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 43
ER -