Organocatalytic Site-Selective Acylation of 10-Deacetylbaccatin III

Masanori Yanagi; Ryo Ninomiya; Yoshihiro Ueda; Takumi Furuta; Takeshi Yamada; Toshiaki Sunazuka; Takeo Kawabata

doi:10.1248/cpb.c16-00037

Special Collection of Papers: Notes

Organocatalytic Site-Selective Acylation of 10-Deacetylbaccatin III

Masanori Yanagi, Ryo Ninomiya, Yoshihiro Ueda, Takumi Furuta, Takeshi Yamada, Toshiaki Sunazuka, Takeo Kawabata

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Keywords: organocatalyst, site-selectivity, acylation, taxane, 10-deacetylbaccatin III, site-selective dimerization

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Supplementary material

2016 Volume 64 Issue 7 Pages 907-912

DOI https://doi.org/10.1248/cpb.c16-00037

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Abstract

Organocatalytic site-selective diversification of 10-deacetylbaccatin III, a key natural product for the semisynthesis of taxol, has been achieved. Various acyl groups were selectively introduced into the C(10)–OH of 10-deacetylbaccatin III. The C(10)–OH selective acylation was also applied to acylative site-selective dimerization of 10-deacetylbaccatin III to provide the structurally defined dimer.

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