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

Mark C. Elliott; James S. Paine

doi:10.1039/B909860G

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Organic & Biomolecular Chemistry

Issue 17, 2009

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

Mark C. Elliott and James S. Paine

Org. Biomol. Chem., 2009, 7, 3455-3462

DOI: 10.1039/B909860G
Received 19 May 2009, Accepted 12 Jun 2009
First published on the web 06 Jul 2009

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Abstract
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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.

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Copies of NMR spectra for compounds 7, 8, 10–16 and 18–26
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Organic & Biomolecular Chemistry

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

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