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The synthesis of a natural product family: from debromoisolaurinterol to the aplysins

The synthesis of a natural product family: from debromoisolaurinterol to the aplysins
The synthesis of a natural product family: from debromoisolaurinterol to the aplysins
Total syntheses of (+/-)-aplysin 1, (+/-)-debromoaplysin 2, (+/-)-isoaplysin 3, (+/-)-aplysinol 4, (+/-)-debromoaplysinol 5, (+/-)-aplysinal 6, (+/-)-isolaurinterol 7 and (+/-)-debromoisolaurinterol 8 are described. Key features are a diastereoselective, sulfur mediated radical cyclisation of diene 12 to give 35; a new radical to polar crossover sequence mediated by Bu3Sn that transforms diene 12 into (+/-)-debromoisolaurinterol 8; and a series of biomimetic cyclisation and oxidation reactions.
terpenes and terpenoids, natural products, radicals and radical reactions, cyclisations, oxygen heterocyclescyclopentanone-aryloximes, rearrangement, (-)-debromoaplysin, sesquiterpenes, (+/-)-aplysin, (-)-aplysin, (+/-)-filiformin, debromoaplysin, provides, yamada
0040-4020
791-804
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 synthesis of a natural product family: from debromoisolaurinterol to the aplysins. Tetrahedron, 57 (4), 791-804. (doi:10.1016/S0040-4020(00)01055-3).

Record type: Article

Abstract

Total syntheses of (+/-)-aplysin 1, (+/-)-debromoaplysin 2, (+/-)-isoaplysin 3, (+/-)-aplysinol 4, (+/-)-debromoaplysinol 5, (+/-)-aplysinal 6, (+/-)-isolaurinterol 7 and (+/-)-debromoisolaurinterol 8 are described. Key features are a diastereoselective, sulfur mediated radical cyclisation of diene 12 to give 35; a new radical to polar crossover sequence mediated by Bu3Sn that transforms diene 12 into (+/-)-debromoisolaurinterol 8; and a series of biomimetic cyclisation and oxidation reactions.

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More information

Published date: 21 January 2001
Keywords: terpenes and terpenoids, natural products, radicals and radical reactions, cyclisations, oxygen heterocyclescyclopentanone-aryloximes, rearrangement, (-)-debromoaplysin, sesquiterpenes, (+/-)-aplysin, (-)-aplysin, (+/-)-filiformin, debromoaplysin, provides, yamada

Identifiers

Local EPrints ID: 19504
URI: http://eprints.soton.ac.uk/id/eprint/19504
ISSN: 0040-4020
PURE UUID: 5f4f028a-500f-43b9-bde2-423d25f50f86
ORCID for D. C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

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Date deposited: 14 Feb 2006
Last modified: 17 Dec 2019 01:59

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Contributors

Author: D. C. Harrowven ORCID iD
Author: M. C. Lucas
Author: P. D. Howes

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