Journal
CHEMICAL & PHARMACEUTICAL BULLETIN
Volume 53, Issue 1, Pages 100-102Publisher
PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.53.100
Keywords
FTY720; immunosuppressive agent; Petasis reaction; boronic acid
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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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