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

A total synthesis of (+/-)-1-desoxyhypnophilin: using ring closing metathesis for the construction of cyclic enones
A total synthesis of (+/-)-1-desoxyhypnophilin: using ring closing metathesis for the construction of cyclic enones
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.
terpenes and terpenoids, natural products, ring closing metathesis, cyclisations, triquinanesorganic-synthesis
0040-4039
8985-8987
Harrowven, D. C.
1c293b83-4291-4301-a7a4-167d6a146d01
Lucas, M. C.
7c5c896a-fdb1-4a54-b5dd-545f0a20392b
Howes, P. D.
23bd5ae7-2e44-47df-96be-51c8c4eee95f
Harrowven, D. C.
1c293b83-4291-4301-a7a4-167d6a146d01
Lucas, M. C.
7c5c896a-fdb1-4a54-b5dd-545f0a20392b
Howes, P. D.
23bd5ae7-2e44-47df-96be-51c8c4eee95f

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).

Record type: Article

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.

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More information

Published date: 11 November 2000
Keywords: terpenes and terpenoids, natural products, ring closing metathesis, cyclisations, triquinanesorganic-synthesis

Identifiers

Local EPrints ID: 18850
URI: http://eprints.soton.ac.uk/id/eprint/18850
ISSN: 0040-4039
PURE UUID: 64310880-3a21-43d2-ba1d-097d6dcf5516

Catalogue record

Date deposited: 15 Dec 2005
Last modified: 15 Jul 2019 19:28

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