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Direct aldol strategy in enantioselective total synthesis of thuggacin B
Akinobu Matsuzawa1, Christopher R Opie, Naoya Kumagai
1Institute of Microbial Chemistry (BIKAKEN), Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan), Fax: (+81) 3-3441-7589 http://www.bikaken.or.jp/research/group/shibasaki/shibasaki-lab/index_e.html; Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan).
Abstract:
An enantioselective total synthesis of thuggacin B, a natural product exhibiting antibiotic activity against Mycobacterium tuberculosis, is described. Asymmetric direct aldol reactions promoted by Cu and Zn catalysts play a pivotal role in constructing four stereogenic centers. The use of direct aldol reactions as the initial steps for the synthesis of two key fragments allowed the construction of the other stereogenic centers through chirality transfer.
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