Synthesis of Arylspiroketals Related to the Papulacandins via Generation of Phthalide Oxycarbenium Ions

Margaret A. Brimble; Vittorio Caprio; Andrew D. Johnston; Matthew Sidford

doi:10.1055/s-2001-13404

PAPER

Synthesis of Arylspiroketals Related to the Papulacandins via Generation of Phthalide Oxycarbenium Ions

Margaret A. Brimble*, Vittorio Caprio, Andrew D. Johnston, Matthew Sidford
Department of Chemistry, University of Auckland, 23 Symonds St., Auckland, New Zealand
Fax: +64(9)3737422; e-Mail: m.brimble@auckland.ac.nz;

Abstract

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Abstract

The nucleophilic addition of allylstannanes to oxycarbenium ions generated from phthalide acetate has been studied. The optimum conditions involve the use of trimethylsilyl trifluoromethanesulfonate in dichloromethane at -78 °C. Hydroboration of the allylated products followed by oxidative cyclization provides an efficient synthesis of arylspiroketals which are closely related to the papulacandins.

Key words

phthalides - oxycarbenium ions - papulacandins - spiroketals - allylstannanes

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References

References and Notes

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