光学纯的(4S, 8R)-和(4S, 8S)-1- 烯-8, 9-二醇的改进合成法

本文提出了一个改进的合成两个光学异构纯的94S)-1- 烯-8, 9-二醇的方法,其优点是简便、有效, 适于克量级制备。

A modified synthesis of opitically pure (4S, 8R)-and (4S, 8S)-p-menth-1-ene-8, 9-diols

Two diastereoisomeric(4S)-p-menth-1-ene-8, 9-diols are important intermediates in the synthesis of Ying Zhao Su D. Their preparation were completed through preparation and isolation of the diol derivatives 6a and 6b. The diol mixture 8 obtained from (S)-(-)-limonene by oxidation with Pb(OAC)~4 was treated with phosgene, followed by bromination to give compounds 6a and 6b, which could be separated by flash chromatography in multigram amount, if necessary, further purified by recrystallization. Deprotection of 6a or 6b gave the title compounds. The 8-C configuration was asigned by comparison with corresponding (4R)-series produet.