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The first total synthesis of (+/-)-1-desoxyhypnophilin

The first total synthesis of (+/-)-1-desoxyhypnophilin
The first total synthesis of (+/-)-1-desoxyhypnophilin
The paper describes the first total synthesis of (+/-)-1-desoxyhypnophilin, a linear triquinane from the East African mushroom Lentinus crinitus which displays promising antimicrobial activity. A key feature is the use of a ring closing metathesis reaction with a tertiary allylic alcohol, in conjunction with a PCC induced oxidative rearrangement, to construct a cyclopentenone.
terpenes and terpenoids, natural products, ring closing metathesis, cyclisations, triquinanesring-closing metathesis, 1, 3-diyl trapping reactions, organic-synthesis, bifunctional reagents, lentinus-crinitus, natural-products, (+/-)-coriolin, hirsutene, construction, efficient
0040-4020
9157-9162
Harrowven, D. C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Lucas, M. C.
7c5c896a-fdb1-4a54-b5dd-545f0a20392b
Howes, P. D.
23bd5ae7-2e44-47df-96be-51c8c4eee95f
Harrowven, D. C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
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. (2001) The first total synthesis of (+/-)-1-desoxyhypnophilin. Tetrahedron, 57 (44), 9157-9162. (doi:10.1016/S0040-4020(01)00899-7).

Record type: Article

Abstract

The paper describes the first total synthesis of (+/-)-1-desoxyhypnophilin, a linear triquinane from the East African mushroom Lentinus crinitus which displays promising antimicrobial activity. A key feature is the use of a ring closing metathesis reaction with a tertiary allylic alcohol, in conjunction with a PCC induced oxidative rearrangement, to construct a cyclopentenone.

Full text not available from this repository.

More information

Published date: 29 October 2001
Keywords: terpenes and terpenoids, natural products, ring closing metathesis, cyclisations, triquinanesring-closing metathesis, 1, 3-diyl trapping reactions, organic-synthesis, bifunctional reagents, lentinus-crinitus, natural-products, (+/-)-coriolin, hirsutene, construction, efficient

Identifiers

Local EPrints ID: 19503
URI: http://eprints.soton.ac.uk/id/eprint/19503
ISSN: 0040-4020
PURE UUID: d7e42bad-604d-48ab-b581-ff341196ffc6
ORCID for D. C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

Catalogue record

Date deposited: 14 Feb 2006
Last modified: 19 Nov 2019 01:59

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