Expedient construction of the vibsanin E core without the use of protecting groups

Ralf Heim; Stefan Wiedemann; Craig M Williams; Paul V Bernhardt

doi:10.1021/ol0501222

Expedient construction of the vibsanin E core without the use of protecting groups

Org Lett. 2005 Mar 31;7(7):1327-9. doi: 10.1021/ol0501222.

Authors

Ralf Heim¹, Stefan Wiedemann, Craig M Williams, Paul V Bernhardt

Affiliation

¹ School of Molecular and Microbial Sciences, University of Queensland, St. Lucia, 4072 Queensland, Australia.

PMID: 15787498
DOI: 10.1021/ol0501222

Abstract

[reaction: see text] The tricyclic core of vibsanin E was constructed without the use of a protecting group in six steps. The El Gaïed Baylis-Hillman variant was key to allowing the Brønsted acid induced tandem cyclization forming rings B and C in one operation.

Publication types

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

MeSH terms

Cyclization
Diterpenes / chemical synthesis*
Diterpenes / chemistry*
Molecular Structure
Viburnum / chemistry

Substances

Diterpenes
vibsanin E