The synthesis of a natural product family: from debromoisolaurinterol to the aplysins
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).
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Description/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.
| Item Type: | Article |
|---|---|
| Related URLs: | |
| Keywords: | terpenes and terpenoids, natural products, radicals and radical reactions, cyclisations, oxygen heterocyclescyclopentanone-aryloximes, rearrangement, (-)-debromoaplysin, sesquiterpenes, (+/-)-aplysin, (-)-aplysin, (+/-)-filiformin, debromoaplysin, provides, yamada |
| Subjects: | Q Science Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| Item ID: | 19504 |
| Date Deposited: | 14 Feb 2006 |
| Last Modified: | 01 Jun 2011 01:47 |
| Contributors: | Harrowven, D. C. (Author) Lucas, M. C. (Author) Howes, P. D. (Author) |
| Date: | 21 January 2001 |
| Status: | Published |
| URI: | http://eprints.soton.ac.uk/id/eprint/19504 |
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