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Issue 1, 2017
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Second-generation total synthesis of aplyronine A featuring Ni/Cr-mediated coupling reactions

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Abstract

Second-generation total synthesis of aplyronine A, a potent antitumor marine macrolide, was achieved using Ni/Cr-mediated coupling reactions as key steps. The overall yield of the second-generation synthetic pathway of aplyronine A was 1.4%, obtained in 38 steps based on the longest linear sequence. Compared to our first-generation synthetic pathway of aplyronine A, the second-generation synthesis greatly improved both the yield and number of steps. In particular, we improved the stereoselectivity in the construction of the C13 stereogenic center and the C14–C15 (E)-trisubstituted double bond using the asymmetric Ni/Cr-mediated coupling reaction. Furthermore, we established efficient reaction conditions for the asymmetric Ni/Cr-mediated coupling reaction between the C21–C28 segment and C29–C34 segment. Thus, this coupling reaction proceeded with an equimolar ratio of each segment.

Graphical abstract: Second-generation total synthesis of aplyronine A featuring Ni/Cr-mediated coupling reactions

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Supplementary files

Article information


Submitted
14 Oct 2016
Accepted
31 Oct 2016
First published
31 Oct 2016

Org. Biomol. Chem., 2017,15, 124-131
Article type
Paper

Second-generation total synthesis of aplyronine A featuring Ni/Cr-mediated coupling reactions

I. Hayakawa, K. Saito, S. Matsumoto, S. Kobayashi, A. Taniguchi, K. Kobayashi, Y. Fujii, T. Kaneko and H. Kigoshi, Org. Biomol. Chem., 2017, 15, 124
DOI: 10.1039/C6OB02241C

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