An efficient Amano PS-catalyzed chemo-, regio- and enantioselective hydrolysis of (±)-2,3-di-O-acetyl-2-C-methyl-d-erythrono-1,4-lactone: a facile preparation of bioactive natural products (−)-saccharinic acid lactone and potassium (2R,3R)-2,3,4-trihydroxy-2-methylbutanoate

Saccharinic acid lactone (−)- 1a is a suitable building block for the synthesis of many bioactive natural products. Amano PS-induced chemo-, regio- and enantioselective hydrolysis of diacetyl lactone (±)- 3 has been carried out to obtain (−)- 1a in 46% yield with 99% ee and diacetyl lactone (+)- 3 in 49% yield with 99% ee. The Amano PS-catalyzed enantioselective acylation of (±)- 1a with vinyl acetate as an acyl donor was relatively less efficient and furnished (−)- 7 in 31% yield with 99% ee and (+)- 1a in 63% yield. The conversion of (−)- 1a to leaf-closing substance 2a and an attempted approach to naturally occurring compounds 1b and 2b have been also described.