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Studies towards the total synthesis of lycoposerramine A. Synthesis of a model for the tetracyclic core

Elliott, Mark Christopher and Paine, James S. 2009. Studies towards the total synthesis of lycoposerramine A. Synthesis of a model for the tetracyclic core. Organic & Biomolecular Chemistry 7 (17) , pp. 3455-3462. 10.1039/b909860g

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Abstract

Lycoposerramine A (1) is a pentacyclic alkaloid isolated in 2001 by Takayama and co-workers. A concise synthesis of a model compound 8 for the tetracyclic core of this natural product is described. Key steps include the desymmetrising free-radical cyclisation of compound 7 to give compound 18 and spirocyclisation of compound 26 to give compound 8. Earlier approaches using a novel high-yielding stereoselective anionic cyclisation of a cyclohexa-1,4-diene are also reported.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Royal Society of Chemistry
ISSN: 1477-0520
Last Modified: 04 Jun 2017 01:55
URI: http://orca.cf.ac.uk/id/eprint/5932

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