Total synthesis of (-)-neovibsanin G and (-)-14-epi-neovibsanin G: Towards the synthesis of 15-O-methylneovibsanin F and 14-epi-15-O-methylneovibsanin F

Mak, Jeffrey Y. W. and Williams, Craig M. (2012) Total synthesis of (-)-neovibsanin G and (-)-14-epi-neovibsanin G: Towards the synthesis of 15-O-methylneovibsanin F and 14-epi-15-O-methylneovibsanin F. European Journal of Organic Chemistry, 2012 10: 2001-2012. doi:10.1002/ejoc.201101796


Author Mak, Jeffrey Y. W.
Williams, Craig M.
Title Total synthesis of (-)-neovibsanin G and (-)-14-epi-neovibsanin G: Towards the synthesis of 15-O-methylneovibsanin F and 14-epi-15-O-methylneovibsanin F
Formatted title
Total synthesis of (–)-neovibsanin G and (–)-14-epi-neovibsanin G: Towards the synthesis of 15-O-methylneovibsanin F and 14-epi-15-O-methylneovibsanin F
Journal name European Journal of Organic Chemistry   Check publisher's open access policy
ISSN 1099-0690
1434-193X
Publication date 2012-04-01
Sub-type Article (original research)
DOI 10.1002/ejoc.201101796
Volume 2012
Issue 10
Start page 2001
End page 2012
Total pages 12
Editor Haymo Ross
Place of publication Weinheim, Germany
Publisher Wiley
Collection year 2013
Language eng
Formatted abstract
The total synthesis of (–)-neovibsanin G and (–)-14-epi-neovibsanin G has been accomplished, establishing the absolute configurations of these caged diterpenes as 11S, and confirming Fukuyama's postulated biosynthesis of the neovibsanins. Synthetic studies towards 15-O-methylneovibsanin F and 14-epi-15-O-methylneovibsanin F were undertaken based on the hypothesis that these methoxy substituted caged neovibsanins were artifacts of isolation, formed by the addition of methanol to the terminal alkenes of neovibsanin G and 14-epi-neovibsanin G. The results strongly suggest, however, that the methoxy caged neovibsanins are true natural products.
Keyword Total synthesis
Natural products
Terpenoids
Vibsanin
Cyclization
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2013 Collection
School of Chemistry and Molecular Biosciences
 
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Created: Wed, 18 Apr 2012, 19:41:43 EST by Lucy O'Brien on behalf of School of Chemistry & Molecular Biosciences