Synthesis of the A–D ring system of the gambieric acids

Clark, J. S. , Romiti, F., Sieng, B., Paterson, L. C., Stewart, A., Chaudhury, S. and Thomas, L. H. (2015) Synthesis of the A–D ring system of the gambieric acids. Organic Letters, 17(19), pp. 4694-4697. (doi:10.1021/acs.orglett.5b02093)

[img] Text
110245.pdf - Accepted Version
Restricted to Repository staff only

3MB

Abstract

The A–D fragment of gambieric acids A and C has been synthesized using an asymmetric Tsuji–Trost allylation reaction to couple the two key segments. The A ring fragment has been prepared by a short and highly efficient route involving diastereoselective Lewis acid mediated alkylation of an acetal. Iterative ring-closing metathesis reactions have been used to construct cyclic ethers and assemble the tricyclic B–D fragment.

Item Type:Articles (Letter)
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Chaudhury, Dr Subhabrata and Clark, Professor Stephen and Paterson, Dr Laura and Thomas, Dr Lynne
Authors: Clark, J. S., Romiti, F., Sieng, B., Paterson, L. C., Stewart, A., Chaudhury, S., and Thomas, L. H.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Organic Letters
Journal Abbr.:Org. Lett.
Publisher:American Chemical Society
ISSN:1523-7060
ISSN (Online):1523-7052
First Published:First published 2015 Organic Letters 17(19):4694-4697

University Staff: Request a correction | Enlighten Editors: Update this record

Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
468241Highly convergent total synthesis of Gambieric acid using iterative and two-directional ring-closing metathesis reactionsStephen ClarkEngineering & Physical Sciences Research Council (EPSRC)EP/F031505/1SCHOOL OF CHEMISTRY