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)

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 Thomas, Dr Lynne and Paterson, Dr Laura
• 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

Project Code	Award No	Project Name	Principal Investigator	Funder's Name	Funder Ref	Lead Dept
46824	1	Highly convergent total synthesis of Gambieric acid using iterative and two-directional ring-closing metathesis reactions	Stephen Clark	Engineering & Physical Sciences Research Council (EPSRC)	EP/F031505/1	SCHOOL OF CHEMISTRY