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Synthesis 2007(5): 643-662  
DOI: 10.1055/s-2007-965915
REVIEW
© Georg Thieme Verlag Stuttgart · New York

Use of Stabilized Phthalide Anion Annulation Reactions in Synthesis: An Update

Kris Rathwell, Margaret A. Brimble*
Department of Chemistry, University of Auckland, 23 Symonds St., Auckland 1142, New Zealand
Fax: +64(9)3737422; e-Mail: m.brimble@auckland.ac.nz;
Further Information

Publication History

Received 1 December 2006
Publication Date:
08 February 2007 (online)

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Abstract

Annulation of stabilized phthalide anions with Michael acceptors provides a powerful tool for the synthesis of quinoid natural products. This review details progress made in this area building on the excellent review of this reaction published in 1995.

  • 1 Background

  • 2 Reaction of Phthalide Anions

  • 2.1 α,β-Unsaturated Esters

  • 2.2 Acyclic α,β-Unsaturated Ketones

  • 2.3 Cyclic α,β-Unsaturated Ketones

  • 2.4 2,5-Cyclohexadienones

  • 2.5 Furanones and Pyranones

  • 2.6 Quinones and Quinone Monoketals

  • 2.7 Arynes

  • 2.8 Other Michael Acceptors

  • 3 Related Annulations

  • 3.1 Homophthalic Anhydrides

  • 3.2 Toluate and Unstabilized Phthalide Anions

  • 4 Conclusion

Key words

Michael addition - quinones - stabilized phthalide anions - natural products - Hauser-Kraus annulation