Approach to the Synthesis of Briarane Diterpenes through a Dianionic Claisen Rearrangement and Ring-Closing Metathesis

被引:16
作者
Crimmins, Michael T. [1 ]
Zhang, Yan [1 ,2 ]
Williams, Philip S. [1 ,3 ]
机构
[1] Univ N Carolina, Kenan Caudill Venable & Murray Labs Chem, Chapel Hill, NC 27599 USA
[2] Idexx Labs, One Idexx Dr, Westbrook, ME 04092 USA
[3] BASF, 26 Davis Dr, Res Triangle Pk, NC 27709 USA
关键词
ASYMMETRIC ALDOL ADDITIONS; QUATERNARY CARBONS; OLEFIN METATHESIS; NATURAL-PRODUCTS; STEREOTETRAD; KETONES; ROUTE;
D O I
10.1021/acs.orglett.7b01806
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of the briarane-brianthein A core has-been accomplished utilizing an extension of the dianionic Ireland-Claisen rearrangement to establish the Cl quaternary carbon and the adjacent C10 ring juncture stereocenters. Two sequential ring-dosing Metathesis reactions were exploited to construct the 6-10 trans fused ring system.
引用
收藏
页码:3907 / 3910
页数:4
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