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

Kris Rathwell; Margaret A. Brimble

doi:10.1055/s-2007-965915

REVIEW

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;

Abstract

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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

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