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A Total Synthesis of (±)PenifulvinA.ppt

发布：2017-07-01约小于1千字共12页下载文档

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Pinnick oxidation Na2RuO4 mediated oxidative cascade cyclization * An Approach to a Bislactone Skeleton: A Total Synthesis of (±)PenifulvinA Penifulvin A, a novel sesquiterpenoid with signficant insecticidal activity against the fall armyworm, which revealed a highly complex dioxa[5.5.5.6]-fenestrane skeleton possessing an intriguing arrang-ement of five contiguous stereogenic centers, in which four rings share a central quaternary carbon, and a γ- and a δ-lactone share a chiral acylal center。 (±)-penifulvin A has been accomplished via a 12-step sequence with an overall yield of 16% 机理： Cp2TiCl2-Zn体系是一种单电子转移试剂，在质子性溶剂THF中，Zn将四价的Cp2TiCl2 还原成三价的Cp2TiCl，然后Cp2TiCl将环氧还原开环。 Baldwin规则 : 环中的原子个数（元数），一般为3-8 ；以exo和endo表示闭环时断键的位置，环内对应endo，环外对应exo ；以tet、trig和dig表示反应中亲电碳的杂化状态，tet对应sp3杂化，trig对应sp2杂化，而dig对应sp杂化。 H H CHO * * * 双内酯结构新型倍半萜化合物，具有杀灭秋粘虫的活性，是含有5个手性碳原子的二氧杂窗烷化合物，四环共用一个中央季碳原子,并且双内酯共用一个缩羰酯

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