Enantioselective total synthesis of (-)-neovibsanin G and (-)-14-epi-neovibsanin G

Jeffrey Y W Mak; Craig M Williams

doi:10.1039/c1cc15995j

Enantioselective total synthesis of (-)-neovibsanin G and (-)-14-epi-neovibsanin G

Chem Commun (Camb). 2012 Jan 7;48(2):287-9. doi: 10.1039/c1cc15995j. Epub 2011 Nov 18.

Authors

Jeffrey Y W Mak¹, Craig M Williams

Affiliation

¹ School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, 4072, Australia.

PMID: 22101234
DOI: 10.1039/c1cc15995j

Abstract

The first total synthesis of vibsane-type diterpenoids neovibsanin G and 14-epi-neovibsanin G has been achieved. Key to this endeavour was a late stage EtAlCl(2) mediated skeletal rich cascade leading to the bicyclo[3.3.1]nonane core in one step.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bridged Bicyclo Compounds / chemical synthesis*
Bridged Bicyclo Compounds / chemistry
Chemistry Techniques, Synthetic*
Diterpenes / chemical synthesis*
Diterpenes / chemistry
Models, Molecular
Stereoisomerism
Viburnum / chemistry*

Substances

Bridged Bicyclo Compounds
Diterpenes
neovibsanin G