20 抗腫瘍性物貭バーノレピン及び関連化合物の合成研究

概要

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Novel cyclopropyl intermediate, type 3, has been selected in the synthetic studies directed toward vernolepin 1, a sesquiterpene bismethylene lactone having antitumor and cytotoxic properties. Construction of A/B cis configuration of vernolepin ring system was achieved by thermodynamic control-base catalized intramolecular cyclization of the malonyl ester, 7-to afford a sole product, 9, whose bromination and subsequent cyclization gave the key intermediate 10. This compound plays remarkable roles not only for the introduction of two hydroxy groups in regio- and stereo-specific manners owing to its rigid ring system but also for protection of the active methine atom. This intermediate has further been converted to compound 19 carrying all of the necessary carbon atoms and to compound 26 possessing the α-cis dihydroxyl groups, respectively. Further studies for the total synthesis of 1 and 2 are now in progress.
天然有機化合物討論会の論文
1976-09-20