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.
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1 Introduction
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2 Initial Studies toward (-)-SNF4435 C and (+)-SNF4435 D
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3 Intramolecular Diels-Alder Cycloadditions of Vinylcyclohexadienes
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4 Lewis Acid Catalyzed Cycloisomerization of Trienoates to Bicyclo[3.1.0]hex-2-enes
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4.1 Total Synthesis of Photodeoxytridachione
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4.2 Total Synthesis of (-)-Crispatene
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5 Total Synthesis of Cyercene A and the Placidenes
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6 Total Synthesis of Aureothin, N-Acetylaureothamine and Aureonitrile
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7 Total Synthesis of Deoxytridachione and Serendipitous Total Synthesis of Ocellapyrone A
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8 Rational Total Synthesis of Ocellapyrone A, Ocellapyrone B, Elysiapyrone A and Elysiapyrone B
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9 Completion of the Total Synthesis of (-)-SNF4435 C and (+)-SNF4435 D
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10 The Polyene Manifold
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11 Outlook
electrocyclic reactions - reaction cascades - biomimetic synthesis - natural products - cross-couplings
