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. 2003 Dec 17;125(50):15433-42.
doi: 10.1021/ja0304953.

Total synthesis of apoptolidin: construction of enantiomerically pure fragments

K C Nicolaou  1 , Konstantina C Fylaktakidou, Holger Monenschein, Yiwei Li, Bernd Weyershausen, Helen J Mitchell, Heng-xu Wei, Prasuna Guntupalli, David Hepworth, Kazuyuki Sugita
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Total synthesis of apoptolidin: construction of enantiomerically pure fragments

K C Nicolaou et al. J Am Chem Soc. .

Abstract

A general strategy for the total synthesis of the antitumor agent apoptolidin (1) is proposed, and the chemical synthesis of the defined key building blocks (4, 5, 6, 8, and 9) in their enantiomerically pure forms is described. The projected total synthesis calls for a dithiane coupling reaction to construct the C(20)-C(21) bond, a Stille coupling reaction to form the C(11)-C(12) bond, and a Yamaguchi macrolactonization to assemble the macrolide ring, as well as two glycosidation reactions to fuse the carbohydrate units onto the molecule. First and second generation syntheses to the required fragments for apoptolidin (1) are described.

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