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).

Download

Full text not available from this repository.

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
ePrint ID: 19504
Date Deposited: 14 Feb 2006
Last Modified: 27 Mar 2014 18:09
URI: http://eprints.soton.ac.uk/id/eprint/19504

Actions (login required)

View Item View Item