Synthesis of a Key Intermediate for the Preparation of FTY720 Analogs

Maiko Hamada; Kunitomo Adachi; Hidemasa Hikawa; Yuusaku Yokoyama

doi:10.1248/cpb.c12-00477

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Synthesis of a Key Intermediate for the Preparation of FTY720 Analogs

Maiko Hamada, Kunitomo Adachi, Hidemasa Hikawa, Yuusaku Yokoyama

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Keywords: fingolimod, KRP-203, palladium, chemoselectivity, cross-coupling

JOURNAL FREE ACCESS

2012 Volume 60 Issue 11 Pages 1395-1398

DOI https://doi.org/10.1248/cpb.c12-00477

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Abstract

A concise synthesis of a useful intermediate 10 for the preparation of fingolimod (FTY-720) analogs was achieved by utilizing a chemoselective Sonogashira reaction of trihalobenzene 12 with alkyne 13. The reaction proceeded with high selectivity to give alkyne 11 containing the dihalobenzene moiety in good yield. Compound 11 was converted into intermediate 10 by hydrogenation without reduction of the halogen atoms.

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