21 共通キラル素子を活用する天然物のエナンチオ選択的合成

概要

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Enantioselective syntheses of a variety of natural products using a chiral glycerin derivative ((S)-1) as a common chiral synthon obtained from D-mannitol have been accomplished. The chiral glycerin derivative ((S)-1) has been converted into γ-substituted γ-butyrolactone or α,γ-disubstituted γ-butyrolactone derivatives (3), via the epoxide (2) or the iodide obtained from the glycerin ((S)-1) acetonide, which in turn alkylated or protonated in highly stereoselective fashion to give stereodefined γ-lactone intermediates. From these intermediates, a variety of natural products, such as secoiridoid monoterpenes (-)-semburin (4) and (-)-isosemburin (5), a corynanthe indole alkaloid (-)-antirhine (6), iboga indole alkaloids (+)- and (-)-cleavamine (7), a carbapenem intermediate (8), an eburnamine indole alkaloid, (-)-eburnamenine (10), a bisabolene sesquiterpene (+)-nuciferal (12), and a physostigma indole alkaloid (-)-physostigmine (13), have been synthesized enantioselectively.
天然有機化合物討論会の論文
1982-09-10