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Paper

Org. Biomol. Chem., 2009, 7, 3455 - 3462, DOI: 10.1039/b909860g

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

Mark C. Elliott and James S. Paine

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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