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

Full Text: HTML

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.

Related Articles:

Efficient synthesis and biological activity of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative

[Ohata, Kohei; Terashima, Shiro Tetrahedron, 2009 , vol. 65, # 11 p. 2244 - 2253]

Application of a Flexible Synthesis of (5 R)-Thiolactomycin To Develop New Inhibitors of Type I Fatty Acid Synthase

[McFadden, Jill M; Frehywot, Gojeb L; Townsend, Craig A Organic letters, 2002 , vol. 4, # 22 p. 3859 - 3862]

Application of a Flexible Synthesis of (5 R)-Thiolactomycin To Develop New Inhibitors of Type I Fatty Acid Synthase

[McFadden, Jill M; Frehywot, Gojeb L; Townsend, Craig A Organic letters, 2002 , vol. 4, # 22 p. 3859 - 3862]

Efficient synthesis of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative

[Ohata, Kohei; Terashima, Shiro Tetrahedron Letters, 2006 , vol. 47, # 16 p. 2787 - 2791]

Efficient synthesis of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative

[Ohata, Kohei; Terashima, Shiro Tetrahedron Letters, 2006 , vol. 47, # 16 p. 2787 - 2791]

More Articles...