Picture of UK Houses of Parliament

Leading national thinking on politics, government & public policy through Open Access research

Strathprints makes available scholarly Open Access content by researchers in the School of Government & Public Policy, based within the Faculty of Humanities & Social Sciences.

Research here is 1st in Scotland for research intensity and spans a wide range of domains. The Department of Politics demonstrates expertise in understanding parties, elections and public opinion, with additional emphases on political economy, institutions and international relations. This international angle is reflected in the European Policies Research Centre (EPRC) which conducts comparative research on public policy. Meanwhile, the Centre for Energy Policy provides independent expertise on energy, working across multidisciplinary groups to shape policy for a low carbon economy.

Explore the Open Access research of the School of Government & Public Policy. Or explore all of Strathclyde's Open Access research...

Tri-substituted cyclooctene synthesis at the limits of relay ring-closing metathesis: a racemic difluorinated analog of fucose

Ashworth, Ian W. and Miles, Jonathan A. L. and Nelson, David J. and Percy, Jonathan M. and Singh, Kuldip. (2009) Tri-substituted cyclooctene synthesis at the limits of relay ring-closing metathesis: a racemic difluorinated analog of fucose. Tetrahedron, 65 (46). pp. 9637-9646. ISSN 0040-4020

Full text not available in this repository.Request a copy from the Strathclyde author

Abstract

A telescoped sequence based on metalated enol acetal chem. allowed the efficient delivery of a ring-closing metathesis (RCM) precursor, which was used to form a cyclooctenone product with a tri-substituted alkenyl group in moderate yield, though a high loading of second generation Grubbs' pre-catalyst was required. A relay RCM precursor was synthesized to deliver the key alkylidene at a higher rate; the catalyst loading required was high, and increasing the reaction temp. simply resulted in the loss of the cyclizing alkylidene by a non-productive cross-metathesis pathway. We were forced to use high diln. conditions to suppress the unwanted CM and secure the cyclooctenone product. The cyclooctenone product could be progressed to analogs of fucose and 6-deoxyidose, e.g. I, by UpJohn dihydroxylation.