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A Short Synthesis of the Factor-Xa Inhibitor DX-9065a using palladium-catalyzed key steps

✍ Scribed by Christiane Kehr; Richard Neidlein; Richard A. Engh; Hans Brandsretter; Ralf Kucznierz; Herbert Leinert; Klaus Marzenell; Klaus Strein; Wolfgang Von Der Saal

Publisher: John Wiley and Sons
Year: 1997
Tongue: German
Weight: 316 KB
Volume: 80
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19970800322

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✦ Synopsis

We describe a new, efficient synthesis of DX-9065a (4), a potent inhibitor of the blood coagulation enzyme factor Xa (fXa) which has previously been prepared in more than 20 steps. We saved approximately 10 steps starting with a Pd-catalyzed cyanation of the triflate 10 of 7-methoxynaphthalen-2-01 (9). After cleavage of the Me0 group with boron tribromide, the triflate 6 was coupled to acrylate 5 in a Heck reaction (+3). The subsequent transformations led to DX-9065a.

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