A new approach to the pseudopterosins using an arene alkylation with a gamma-methylene-gamma-butyrolactone


Harrowven, D. C., Wilden, J. D., Tyte, M. J., Hursthouse, M. B. and Coles, S. J. (2001) A new approach to the pseudopterosins using an arene alkylation with a gamma-methylene-gamma-butyrolactone. Tetrahedron Letters, 42, (6), 1193-1195. (doi:10.1016/S0040-4039(00)02207-3).

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Description/Abstract

A short and practical route to the tricyclic core of an unnatural pseudopterosin diastereoisomer is presented. Key features are an arene alkylation with a gamma -methylene-gamma -butyrolactone, viz. 10 --> 14, and an elaborate reduction sequence 14 --> 17 which both proceed diastereoselectively.

Item Type: Article
Digital Object Identifier (DOI): doi:10.1016/S0040-4039(00)02207-3
Related URLs:
Keywords: annulation, cyclisation, lactones, natural products, terpenes and terpenoidsenantioselective synthesis, stereochemistry, route, functionality, intermediate, elisabethae, chemistry, aglycone
Subjects: Q Science
Q Science > QD Chemistry
Divisions : University Structure - Pre August 2011 > School of Chemistry
ePrint ID: 19511
Accepted Date and Publication Date:
Status
5 February 2001Published
Date Deposited: 14 Feb 2006
Last Modified: 31 Mar 2016 11:36
URI: http://eprints.soton.ac.uk/id/eprint/19511

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