A concise approach to the core structures of pinnaic acid and halichlorine

Sung-Hyun Yang; G. R. Clark; Vittorio Caprio

doi:10.1039/B903904J

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Organic & Biomolecular Chemistry

Issue 14, 2009

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A concise approach to the core structures of pinnaic acid and halichlorine

Sung-Hyun Yang , G. R. Clark and Vittorio Caprio

Org. Biomol. Chem., 2009, 7, 2981-2990

DOI: 10.1039/B903904J
Received 25 Feb 2009, Accepted 15 May 2009
First published on the web 15 Jun 2009

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An efficient and flexible synthetic approach to the core structures of pinnaic acid and halichlorine is described using spirocyclic nitrone 4 as a key intermediate. 1,3-Dipolar cycloaddition of 4 with dipolarophile 8 provides access to the azaspirocyclic core of pinnaic acid 5 while the spiroquinolizidine core of halichlorine 6 has been synthesised via cycloaddition of 4 with dipolarophile 29. Nitrone 4 is accessed by oxidative ring opening of isoxazolidine 9. The utility of this synthetic strategy in the synthesis of C5 substituted analogues of pinnaic acid is also demonstrated.

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Organic & Biomolecular Chemistry

A concise approach to the core structures of pinnaic acid and halichlorine

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