6-烯-8-羰基-1-叔丁氧基羰基氮杂螺[4,4]壬烷的合成

Synthesis of 1-Aza-1-(t-butoxycarbonyl)-8-oxo-spiro[4,4]non-6-ene

以烯丙基脯氨酸甲酯(1)为起始原料,经7步反应以42%的总收率得到了三尖杉碱合成中的重要中间体6-烯-8-羰基-1-叔丁氧基羰基氮杂螺[4,4]壬烷(7).关键反应为构筑螺环季碳的[2,3]斯蒂文森重排(Stevens rearrangement)及烯丙基双键加氧的酸内酯化反应(Acid-lactonization reaction).

1-Aza-1-（t-butoxycarbonyl）-8-oxo-spiro[4,4]non-6-ene （7）,one of the key intermediates in the preparation of cephalotaxine,was conveniently synthesized in 42% overall yield with the Stevens rearrangement and acid-lactonization as key steps.