White David E, Stewart Ian C, Grubbs Robert H, Stoltz Brian M
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
J Am Chem Soc. 2008 Jan 23;130(3):810-1. doi: 10.1021/ja710294k. Epub 2007 Dec 29.
Described in this report is the first total synthesis of elatol, a halogenated sesquiterpene in the chamigrene natural product family. The key disconnections in our synthetic approach include an enantioselective decarboxylative allylation to form the all-carbon quaternary stereocenter and a ring-closing olefin metathesis to concomitantly form the spirocyclic core as well as the fully substituted chlorinated olefin. This strategy represents a general platform for accessing the chamigrene natural product family, as demonstrated by the synthesis of (+)-laurencenone B as an intermediate in our route.
本报告描述了对愈创木酚(一种愈创木烷天然产物家族中的卤化倍半萜)的首次全合成。我们合成方法中的关键切断步骤包括对映选择性脱羧烯丙基化反应以形成全碳季立体中心,以及闭环烯烃复分解反应以同时形成螺环核心以及完全取代的氯化烯烃。该策略代表了一个用于合成愈创木烷天然产物家族的通用平台,正如我们路线中作为中间体的(+)-月桂烯酮B的合成所证明的那样。