An efficient Amano PS-catalyzed chemo-, regio- and enantioselective hydrolysis of (±)-2,3-di-O-acetyl-2-C-Methyl-D-erythrono-1,4-lactone (cas 18465-71-9): a facile preparation of bioactive natural products (−)-saccharinic acid lactone and potassium (2R,3R)-2,3,4-trihydroxy-2-methylbutanoate☆

Add time:09/04/2019    Source:sciencedirect.com

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.

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