Efficient Chiral Route to a Key Building Block of 1,25-Dihydroxyvitamin D3 via Lipase-Mediated Resolution

Seiichi Takano; Takahiro Yamane; Michiyasu Takahashi; Kunio Ogasawara

doi:10.1055/s-1992-21362

Synlett 1992; 1992(5): 410-412
DOI: 10.1055/s-1992-21362

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Efficient Chiral Route to a Key Building Block of 1,25-Dihydroxyvitamin D₃ via Lipase-Mediated Resolution

Seiichi Takano^* , Takahiro Yamane, Michiyasu Takahashi, Kunio Ogasawara

^*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980, Japan

Abstract

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Racemic ethyl 5-hydroxy-1-cyclopentenecarboxylate [(±)-4] was resolved with complete enantiospecificity via kinetic acetylation in tert-butyl methyl ether in the presence of lipase PS which furnished optically pure (R)-acetate [(R)-5] and (S)-alcohol [(S)-4] both in nearly quantitative yields after silica gel column chromatography. (R)-Alcohol [(R)-4] obtained from (R)-5 was transformed into 1-ethynylbicyclo[3.1.0]hexan-2-one (3), a key building block of 1,25-dihydroxyvitamin D₃ (1), in eight steps in 30% overall yield.

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