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doi:10.1016/S0040-4039(00)01165-5 
Copyright © 2000 Elsevier Science Ltd. All rights reserved.
Synthesis of (+)-discodermolide and analogues by control of asymmetric induction in aldol reactions of γ-chiral (Z)-enals
Received 20 June 2000;
accepted 12 July 2000.
Available online 18 August 2000.
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Abstract
The boron-mediated aldol reactions of the (Z)-enals 3 and 7 proceed with high levels of 1,4-stereoinduction arising from the γ-substituent. Reagent control from (+)-Ipc2BCl can be used effectively to overturn this substrate bias, thus enabling the stereocontrolled formation of (+)-discodermolide (1) and related analogues 15–18.
Author Keywords: discodermolide; boron aldol; isopinocampheyl; anticancer; remote stereoinduction
