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Synlett 2006(14): 2295-2316  
DOI: 10.1055/s-2006-949627
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© Georg Thieme Verlag Stuttgart · New York

Mapping the Chemistry of Highly Unsaturated Pyrone Polyketides

Aubry K. Miller, Dirk Trauner*
Department of Chemistry, University of California Berkeley, Berkeley, California 94720-1460, USA
Fax: +1(510)6439480; e-Mail: trauner@cchem.berkeley.edu;
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Publication History

Received 13 April 2006
Publication Date:
24 August 2006 (online)

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Abstract

Highly unsaturated pyrone polyketides (‘HUPPs’) are a growing family of natural products derived from polyene precursors, often through pericyclic or ionic reaction cascades. We describe our extensive studies on this class of compounds, which have so far resulted in the total synthesis of 17 of its members.

  • 1 Introduction

  • 2 Initial Studies toward (-)-SNF4435 C and (+)-SNF4435 D

  • 3 Intramolecular Diels-Alder Cycloadditions of Vinylcyclohexadienes

  • 4 Lewis Acid Catalyzed Cycloisomerization of Trienoates to Bicyclo[3.1.0]hex-2-enes

  • 4.1 Total Synthesis of Photodeoxytridachione

  • 4.2 Total Synthesis of (-)-Crispatene

  • 5 Total Synthesis of Cyercene A and the Placidenes

  • 6 Total Synthesis of Aureothin, N-Acetylaureothamine and Aureonitrile

  • 7 Total Synthesis of Deoxytridachione and Serendipitous ­Total Synthesis of Ocellapyrone A

  • 8 Rational Total Synthesis of Ocellapyrone A, Ocellapyrone B, Elysiapyrone A and Elysiapyrone B

  • 9 Completion of the Total Synthesis of (-)-SNF4435 C and (+)-SNF4435 D

  • 10 The Polyene Manifold

  • 11 Outlook

Key words

electrocyclic reactions - reaction cascades - biomimetic synthesis - natural products - cross-couplings