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

Changjin Lim; Jungmin Ahn; Jaehoon Sim; Hwayoung Yun; Joonseong Hur; Hongchan An; Jaebong Jang; Seungbeom Lee; Young Ger Suh

doi:10.1039/c7cc08329g

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

Changjin Lim
, Jungmin Ahn
, Jaehoon Sim
, Hwayoung Yun
, Joonseong Hur
, Hongchan An
, Jaebong Jang
, Seungbeom Lee
, Young Ger Suh

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

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.

Original language	English
Pages (from-to)	467-470
Number of pages	4
Journal	Chemical Communications
Volume	54
Issue number	5
DOIs	https://doi.org/10.1039/c7cc08329g
Publication status	Published - 2018

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Publisher Copyright:
This journal is © 2018 The Royal Society of Chemistry.

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title = "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.",

author = "Changjin Lim and Jungmin Ahn and Jaehoon Sim and Hwayoung Yun and Joonseong Hur and Hongchan An and Jaebong Jang and Seungbeom Lee and Suh, \{Young Ger\}",

note = "Publisher Copyright: This journal is {\textcopyright} 2018 The Royal Society of Chemistry.",

year = "2018",

doi = "10.1039/c7cc08329g",

language = "English",

volume = "54",

pages = "467--470",

journal = "Chemical Communications",

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T1 - Total synthesis of (+)-brasilenyne

T2 - Via concise construction of an oxonane framework containing a 1,3- cis, cis -diene

AU - Lim, Changjin

AU - Ahn, Jungmin

AU - Sim, Jaehoon

AU - Yun, Hwayoung

AU - Hur, Joonseong

AU - An, Hongchan

AU - Jang, Jaebong

AU - Lee, Seungbeom

AU - Suh, Young Ger

PY - 2018

Y1 - 2018

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85040603632

U2 - 10.1039/c7cc08329g

DO - 10.1039/c7cc08329g

M3 - Article

C2 - 29255829

AN - SCOPUS:85040603632

SN - 1359-7345

VL - 54

SP - 467

EP - 470

JO - Chemical Communications

JF - Chemical Communications

IS - 5

ER -

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

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