Synthesis of Natural Products with Polycyclic Systems

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概要

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• Herein we present our unique strategies to synthesize natural products. To prepare mersicarpine, an atypical indole alkaloid, our procedure features an Eschenmoser–Tanabe fragmentation to synthesize an alkyne unit, a combination of a Sonogashira coupling and a gold(III) catalyzed cyclization to construct the indole skeleton, and a one-pot process to arrange the cyclic imine and the hemiaminal moieties. Additionally, we synthesized a frog poison, histrionicotoxin, via a chirality transfer from an allenylsilane to prepare a pseudosymmetrical dienyne, dienyne metathesis to produce an optically active bicyclo [5.4.0] system, and an asymmetric propargylation. To synthesize lyconadin A, a Lycopodium alkaloid, a combination of an aza-Prins reaction and electrocyclic ring opening constructed the highly fused tetracyclic compound. The synthesis of isoschizogamine features a facile construction of the carbon framework through a Wagner–Meerwein rearrangement, a tandem metathesis, a stereoselective rhodium-mediated 1,4-addition of an arylboronic acid, and a ring-closing metathesis via a hemiaminal ether.

• 公益社団法人 日本薬学会の論文

著者

• Yokoshima Satoshi

  Graduate School Of Pharmaceutical Sciences The University Of Tokyo

• Yokoshima Satoshi

  Graduate School of Pharmaceutical Sciences, Nagoya University

関連論文

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• A Novel Oxidative Transformation of α-Aminonitriles to Amides
• Synthesis of Natural Products with Polycyclic Systems

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