TOTAL SYNTHESIS OF DL-VEATCHINE AND DL-GARRYINE
TOTAL SYNTHESIS OF DL-VEATCHINE AND DL-GARRYINE
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DOI：
10.1021/ja00982a037
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发表时间：
1967-01-01
影响因子：
15
通讯作者：
SUGASAWA, T
中科院分区：
文献类型：
--
作者：
NAGATA, W;NARISADA, M;SUGASAWA, T
本文报道了外消旋体维钦碱和加里宁的全合成。合成从五环化合物4开始，该化合物4是合成阿替辛的相同中间体。本工作的主要问题是将化合物4中的叶枝藻烯型的CD桥环体系转化为化合物13中的贝壳杉烯型的相反桥环构型。对于这种转换涉及瓦格纳-Meerwein型重排两条路线的建立。将烯丙醇官能团引入D环中以与阿替辛合成中所用相同的方式进行。本合成的最终化合物是cZZ-二氢野豌豆碱（24 c）。24 c转化为garryine和进一步的veatchine通过几个步骤的合成已经记录在自然系列。
The total synthesis of veatchine and garryinein a racemic form is described. The synthesis is started from the pentacyclic compound 4, the same intermediate for the synthesis of atisine. The major problem treated in the present work is toconvert the CD bridged ring system of the phyllocladene type in 4 into the opposite bridge configuration of the kaurene type in 13. For this conversion two routes involving the Wagner-Meerwein type rearrangement are established. Introduction of the allyl alcohol function into the D ring is carried out in the same manner as employed in the atisine synthesis. The final compound of the present synthesis is cZZ-dihydroveatchine (24c). The transformation of 24c to garryine and further to veatchine by a few-steps synthesis is already recorded in the natural series.