Chemoenzymatic Carbon-Carbon Bond Formation Leading to Non-carbohydrate Derivative. Stereoselective Synthesis of Pentamycin C-11-C-16 Fragment

Masayuki SHIMAGAKI; Hiroaki MUNESHIMA; Masahide KUBOTA; Takeshi OISHI

doi:10.1248/cpb.41.282

Masayuki SHIMAGAKI, Hiroaki MUNESHIMA, Masahide KUBOTA, Takeshi OISHI

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Keywords: aldolase, pentamycin, asymmetric aldol condensation, 7-O-benzyl-6-deoxy-D-xyloheptulose, α-hydroxyaldehyde, dihydroxyacetone phosphate

JOURNAL FREE ACCESS

1993 Volume 41 Issue 2 Pages 282-286

DOI https://doi.org/10.1248/cpb.41.282

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Abstract

Chemoenzymatic formation of 8 from an aldehyde 5 and dihydroxyacetone phosphate 6 was achieved by the use of fructose 1, 6-diphosphate aldolase as a catalyst. Transformation of 8 to 20, corresponding to pentamycin C-11-C-16 fragment, was accomplished via 18a and 18b by chemical processes.

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