光学活性化合物多羟基庚酸乙酯的合成

The Synthesis of the Optically Active Ethyl Polyhydroxy Heptanoate

以不对称环氧化和双羟化反应为构筑手性碳的关键步骤,首次合成了(+)-(2R,3S,4S,5S)-6-甲基-4,5-环氧-2,3-二羟基-庚酸乙酯(5)和(-)-(2R,3S,4R,5S)-6-甲基-2,3,4,5-四羟基-庚酸乙酯(11).找到一条适宜于该类化合物合成的简便有效且立体选择性好的合成路线.初步生物活性测试表明,化合物5,11对HL60细胞具有抑制活性.

The first synthesis of ethyl （＋）-（2R,3S,4S,5S）-4,5-epoxy-2,3-dihydroxy-6-methyl heptanoate （5） and ethyl （-）-（2R,3S,4R,5S）-2,3,4,5-tetrahydroxy-6-methyl heptanoate （11） was achieved and the key steps involved the construction of chiral carbon centers by the asymmetric epoxidation and dihydroxylation. This efficiently concise strategy has better stereochemistry and is adapted to the synthesis of polyhydroxyl fatty acid analogues. The primary tests of compounds 5 and 11 showed better inhibitory activities against HL60 cell line.