27 抗発癌プロモーターSarcophytol-Aの全合成(ポスター発表の部)

概要

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Sarcophytol-A (1), a cembrane type diterpenoid isolated from an Okinawan soft coral, has been shown to be a potent antitumor promoter in a two-stage carcinogenesis model, and to exhibit antitumor activity. The first total synthesis of 1 was accomplished in a highly stereo- and enantioselective manner, starting from commercially available (E,E)-Farnesol (5) or Geraniol(20). The synthesis involved 1) the newly developed, highly stereoselective Horner-Emmons condensation (Z:E>35:1) of 6 with phosphonatenitrile (16), 2) the modified macrocyclization based on intramolecular alkylation of cyanohydrin trimethylsilyl ether (18), 3) the highly enantioselective reduction (93% e.e.) of macrocyclic ketone (2) with chiral lithium aluminum hydride, and 4) the highly stereoselective mercury-free Claisen sequence (E>99%) using acetal(26).
天然有機化合物討論会の論文
1991-09-07