Pentafulvene for the Synthesis of Complex Natural Products: Total Syntheses of (±)‐Pallambins A and B |
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| Authors: | Christian Ebner Prof Dr Erick M Carreira |
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| Institution: | Laboratorium für Organische Chemie, ETH Zürich, HCI H335, Vladimir‐Prelog‐Weg 3, 8093 Zürich (Switzerland) http://www.carreira.ethz.ch |
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| Abstract: | The first total syntheses of pallambins A and B are enabled by the use of pentafulvene in an unprecedented Diels–Alder reaction. After elaboration of the adduct through chemoselective cyclopropanation, strategic C? H insertion affords the dense tetracyclic core of the natural products. 1,3‐Dipolar cycloaddition and palladium(II)‐catalyzed alkoxycarbonylation were leveraged for the construction of the hexacyclic scaffold en route to both natural products. |
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| Keywords: | C H insertion cycloaddition natural products small‐ring systems total synthesis |
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