A convenient synthesis of immunosuppressive agent FTY720 using the petasis reaction

S Sugiyama, S Arai, M Kiriyama, K Ishii

Index: Sugiyama, Shigeo; Arai, Satoshi; Kiriyama, Matsuri; Ishii, Keitaro Chemical and Pharmaceutical Bulletin, 2005 , vol. 53, # 1 p. 100 - 102

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Citation Number: 32

Abstract

A convenient synthesis of immunosuppressive agent FTY720 (1) using the Petasis reaction was developed. 4-Octylbenzaldehyde (9) was converted into 1-ethenyl-4-octylbenzene (11) by two-step synthesis. Hydroboration of 11 using catecholborane and hydrolysis gave (E)-2- (4-octylphenyl) vinylboronic acid (4). The Petasis reaction of 4, dihydroxyacetone (3), and benzylamine following catalytic hydrogenation afforded FTY720 (1).

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