Enantioselective Desymmetrization of FTY720

Hidemasa Hikawa; Maiko Hamada; Yuka Uchida; Shoko Kikkawa; Yuusaku Yokoyama; Isao Azumaya

doi:10.1248/cpb.c14-00462

Notes

Enantioselective Desymmetrization of FTY720

Hidemasa Hikawa , Maiko Hamada, Yuka Uchida, Shoko Kikkawa, Yuusaku Yokoyama, Isao Azumaya

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Keywords: desymmetrization, FTY720, CuCl₂, asymmetric synthesis, tetraphenylbisoxazoline

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Supplementary material

2014 Volume 62 Issue 10 Pages 1041-1044

DOI https://doi.org/10.1248/cpb.c14-00462

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Abstract

A method for enantioselective desymmetrization of N-Ac and N-Boc-FTY720 by nonenzymatic asymmetric acylation was developed. Effective enantioselective monobenzoylation using benzoyl chloride in the presence of the tetraphenylbisoxazoline (L2)–CuCl₂ complex gave the desired products 3a and 3b in 52–62% yield with 64% ee.

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