Issue 5, 2018

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

Abstract

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
29 okt 2017
Accepted
11 dec 2017
First published
11 dec 2017

Chem. Commun., 2018,54, 467-470

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

C. Lim, J. Ahn, J. Sim, H. Yun, J. Hur, H. An, J. Jang, S. Lee and Y. Suh, Chem. Commun., 2018, 54, 467 DOI: 10.1039/C7CC08329G

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