Total synthesis of (+)-brasilenyne via concise construction of an oxonane framework containing a 1,3-cis,cis-diene

The enantioselective total synthesis of (+)-brasilenyne has been accomplished. The key features of the synthesis include the convergent preparation of a highly functionalized endocyclization precursor via selective epoxide opening, the construction of an oxonene skeleton through perfect regioselecti...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2018, Vol.54 (5), p.467-470
Main Authors: Lim, Changjin, Ahn, Jungmin, Sim, Jaehoon, Yun, Hwayoung, Hur, Joonseong, An, Hongchan, Jang, Jaebong, Lee, Seungbeom, Suh, Young-Ger
Format: Article
Language:English
Subjects:
Synthesis
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Summary:The enantioselective total synthesis of (+)-brasilenyne has been accomplished. The key features of the synthesis include the convergent preparation of a highly functionalized endocyclization precursor via selective epoxide opening, the construction of an oxonene skeleton through perfect regioselective Pd(0)-catalyzed endocyclization, and the installation of a 1,3-cis,cis-diene unit via a decarboxylative photophenylselenylation and site-selective selenoxide elimination sequence.
ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc08329g