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Dr. Masaru Enomoto, Dr. Akira Morita and Prof. Dr. Shigefumi Kuwahara Total Synthesis of the Tremorgenic Indole Diterpene Paspalinine Angewandte Chemie International Edition 51

Article first published online: 7 NOV 2012 | DOI: 10.1002/anie.201206299

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Succinct and stereoselective: A high-yielding two-step indole ring installation comprising the Stille cross-coupling and a PdII-mediated oxidative heterocyclization was exploited in a concise total synthesis of paspalinine. The trans-anti-trans CDE fused ring system of the heptacyclic natural product was established highly stereoselectively through hydroxy-directed cyclopropanation and allylic selenoxide rearrangement.

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