Tetrahedron letters

Lipase-catalyzed kinetic resolution of thiotetronic acid derivatives bearing a chiral quaternary carbon: total synthesis of (R)-thiolactomycin and its O-analogue

K Toyama, T Tauchi, N Mase, H Yoda, K Takabe

Index: Toyama, Ken-ichi; Tauchi, Tetsuo; Mase, Nobuyuki; Yoda, Hidemi; Takabe, Kunihiko Tetrahedron Letters, 2006 , vol. 47, # 40 p. 7163 - 7166

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Citation Number: 12

Abstract

We have developed a chemoenzymatic synthesis of (R)-thiolactomycin (1) having a chiral quaternary carbon atom at C5. In the kinetic resolution of the thiotetronic acid precursor 4, both enantiomers were obtained with high enantiomeric excess by use of Chirazyme® L-2. Chemical transformations of the (R)-alcohol 4 provided the chiral (R)-thiolactomycin (1) in 36% yield in five steps.