Asymmetric [4+3] cycloadditions between vinylcarbenoids and dienes: Application to the total synthesis of the natural product (-)-5-epi-Vibsanin E

Schwartz, Brett D., Denton, Justin R., Lian, Yajing, Davies, Huw M. L. and Williams, Craig M. (2009) Asymmetric [4+3] cycloadditions between vinylcarbenoids and dienes: Application to the total synthesis of the natural product (-)-5-epi-Vibsanin E. Journal of the American Chemical Society, 131 23: 8329-8332. doi:10.1021/ja9019484


Author Schwartz, Brett D.
Denton, Justin R.
Lian, Yajing
Davies, Huw M. L.
Williams, Craig M.
Title Asymmetric [4+3] cycloadditions between vinylcarbenoids and dienes: Application to the total synthesis of the natural product (-)-5-epi-Vibsanin E
Formatted title
Asymmetric [4+3] cycloadditions between vinylcarbenoids and dienes: Application to the total synthesis of the natural product (-)-5-epi-Vibsanin E
Journal name Journal of the American Chemical Society   Check publisher's open access policy
ISSN 0002-7863
Publication date 2009-05-15
Year available 2009
Sub-type Article (original research)
DOI 10.1021/ja9019484
Open Access Status DOI
Volume 131
Issue 23
Start page 8329
End page 8332
Total pages 4
Editor Peter J Stang
Place of publication United States
Publisher American Chemical Society
Language eng
Subject C1
0305 Organic Chemistry
970103 Expanding Knowledge in the Chemical Sciences
Abstract The total synthesis of (-)-5-epi-vibsanin E (2) has been achieved in 18 steps. The synthesis combines the rhodium-catalyzed [4 + 3] cycloaddition between a vinylcarbenoid and a diene to rapidly generate the tricyclic core with an effective end game strategy to introduce,the remaining side-chains. The [4 + 3] cycloaddition occurs by a cyclopropanation to form a divinylcyclopropane followed by a Cope rearrangement to form a cycloheptadiene. The quaternary stereogenic center generated in the process can be obtained with high asymmetric induction when the reaction is catalyzed by the chiral dirhodium complex, Rh(2)(S-PTAD)(4).
Keyword Viburnum-odoratissimum Ker
Q-Index Code C1
Q-Index Status Confirmed Code
Grant ID DP0666855
GM080337
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: 2010 Higher Education Research Data Collection
School of Chemistry and Molecular Biosciences
 
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Created: Thu, 03 Sep 2009, 17:53:01 EST by Mr Andrew Martlew on behalf of School of Chemistry & Molecular Biosciences