Organic Letters
Organic Letters
5 years ago

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

Approach to the Synthesis of Briarane Diterpenes through a Dianionic Claisen Rearrangement and Ring-Closing Metathesis
Michael T. Crimmins, Yan Zhang, Philip S. Williams
The synthesis of the briarane–brianthein A core has been accomplished utilizing an extension of the dianionic Ireland–Claisen rearrangement to establish the C1 quaternary carbon and the adjacent C10 ring juncture stereocenters. Two sequential ring-closing metathesis reactions were exploited to construct the 6–10 trans fused ring system.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01806

DOI: 10.1021/acs.orglett.7b01806

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