Synthesis of the Tetracyclic Core of the Tetrapetalones through Transannular Oxidative [4+3] Cyclization

Authors

  • Xiang Wang,

    1. Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-353-6466
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  • John A. Porco Jr. Prof.

    1. Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-353-6466
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Errata

This article is corrected by:

  1. Errata: Synthesis of the Tetracyclic Core of the Tetrapetalones through Transannular Oxidative [4+3] Cyclization Volume 45, Issue 40, 6607, Article first published online: 10 October 2006

  • We thank Dr. J. Lee (Boston University) for assistance with NMR experiments and the National Institutes of Health (GM-62842) for research support.

Abstract

original image

A convergent strategy involving a base-mediated silyl transfer/acylation for fragment coupling and a tandem process consisting of nitro reduction and acyl transfer can be employed to construct strained, bicyclic macrolactams (see scheme). The tetracyclic core of the tetrapetalones, which are effective lipoxygenase inhibitors, can be prepared by using an IIII-promoted cyclization.

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