A total synthesis of (+/-)-1-desoxyhypnophilin: using ring closing metathesis for the construction of cyclic enones


Harrowven, D. C., Lucas, M. C. and Howes, P. D. (2000) A total synthesis of (+/-)-1-desoxyhypnophilin: using ring closing metathesis for the construction of cyclic enones. Tetrahedron Letters, 41, (46), 8985-8987. (doi:10.1016/S0040-4039(00)01595-1).

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Description/Abstract

The paper describes the first total synthesis of (+/-)-1-desoxyhypnophilin, a linear triquinane isolated from the East African mushroom Lentinus crinitus which displays promising antimicrobial activity. The key strategic feature is a new cyclopentannulation method for appending cycloalkenones onto ketones involving sequential use of a ring closing metathesis reaction with a tertiary allylic alcohol and a PCC induced oxidative rearrangement.

Item Type: Article
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Keywords: terpenes and terpenoids, natural products, ring closing metathesis, cyclisations, triquinanesorganic-synthesis
Subjects: Q Science
Q Science > QD Chemistry
Divisions: University Structure - Pre August 2011 > School of Chemistry
ePrint ID: 18850
Date Deposited: 15 Dec 2005
Last Modified: 27 Mar 2014 18:08
URI: http://eprints.soton.ac.uk/id/eprint/18850

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