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Published on: September 9, 2016
Total synthesis of (-)-apicularen A
Sanjay S Palimkar1, Jun'ichi Uenishi
1Kyoto Pharmaceutical University, Misasagi Yamashina, Kyoto 607-8412, Japan.
Abstract:
A convergent total synthesis of (-)-apicularen A, a highly cytostatic 12-membered macrolide, has been accomplished. The key steps include assembling of iodoalkene 8 and aldehyde 9 by Nozaki-Hiyama-Kishi (NHK) coupling, stereospecific construction of 2,6-trans-disubstituted dihydropyran by Pd(II)-catalyzed 1,3-chirality transfer reaction, and Yamaguchi macrolactonization. Introduction of the (2Z,4Z)-heptadienamide moiety in the side chain by an efficient Cu(I)-mediated coupling completed the total synthesis.
