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Synfacts 2011(2): 0124-0124  
DOI: 10.1055/s-0030-1259210
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (+)- and (-)-Fluvastatin

Contributor(s): Philip Kocienski
J. T. Zacharia, T. Tanaka, M. Hayashi*
Kobe University, Japan
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Publikationsdatum:
19. Januar 2011 (online)

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Significance

Fluvastatin is an HMG-CoA reductase inhibitor marketed as a racemate. The key step in the synthesis depicted was the enantio­selective addition of diketene E to the aldehyde C mediated by the enantiopure Schiff base D and ­titanium isopropoxide. The stoichiometric version of the reaction shown gave the α-hydroxy ketone H in 78% yield (er = 96:4), whereas 10 mol% of (S)-D delivered H in 70% yield (er = 87:13).