42 光学活性ブチロラクトン誘導体をSynthonとして用いる合成研究 : 天然抗腫瘍性リグナン類の不斉合成

概要

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A new mothodology for the chiral synthesis of natural products was developed by the novel approach to use optically active butyrolactone derivative (1), which is easily available from L-glutamic acid, as a chiral synthon. This procedure is cnostituted from the two key steps, the first is the creation of new chiral centers (2) on 1 and the second is the removal of the original chiral center (3) derived from 1. Applying this new mwthodology to the chiral synthesis of pharmacologically active lignan lactones, the key intermediate (S)-11, as well as its antipode (R)-11 were successufully synthesized. (S)- and (R)-11 were shown to be the key intermediates by the conversion into several optically active lignan lactones. The chiral butenolide (18) was also shown to be highly usefull for the synthesis of the chiral lignan lactones, giving the very high selectivity. In addition to the above fundamental methodology, the stereo-selective synthesis of the antitumor burseran (28) and the determination of the stereochemical structure of natural burseran were achived. The novel isomerization reaction of antileukemic steganacin skeleton and the first synthesis of stegane (32), the parent skeleton of steganacin (4), were also achived.
天然有機化合物討論会の論文
1979-09-20