Total Synthesis of (+)-Cyperolone

Total Synthesis of (+)-Cyperolone
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DOI:
10.1021/ol300058t
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发表时间:
2012-03-02
期刊:
影响因子:
5.2
通讯作者:
Kirsch, Stefan F.
Kirsch, Stefan F.
中科院分区:
化学1区
文献类型:
--
作者:
Klahn, Philipp;Duschek, Alexander;Kirsch, Stefan F.

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报道了香附子中桉烷衍生的倍半萜类化合物(+)-香附醇酮的全合成。从(R)-(-)-香芹酮开始,通过15步序列完成从头合成。该合成路线的特征在于铂催化的环异构化以从3-甲硅烷基氧基-1,5-烯炔中间体快速构建双环核。
The total synthesis of (+)-cyperolone, an eudesmane-derived sesquiterpenoid from Cyperus rotundus, Is described. The de novo synthesis was accomplished via a 15 step sequence starting from (R)-(-)-carvone. The synthetic route features a platinum-catalyzed cycloisomerization to rapidly construct the bicyclic core from a 3-silyloxy-1,5-enyne intermediate.