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Total Synthesis of (−)‐Daphenylline

2016; Wiley; Volume: 55; Issue: 20 Linguagem: Inglês

10.1002/anie.201601958

1521-3773

Ryosuke Yamada, Yohei Adachi, Satoshi Yokoshima, Tohru Fukuyama,

Synthetic Organic Chemistry Methods

Abstract Total synthesis of (−)‐daphenylline, a hexacyclic Daphniphyllum alkaloid, was achieved. Construction of the tricyclic DEF ring system was initiated by asymmetric Negishi coupling followed by an intramolecular Friedel–Crafts reaction. Installation of a side chain onto the tricyclic core was carried out through Sonogashira coupling, stereocontrolled Claisen rearrangement by taking advantage of the characteristic conformation of the tricyclic DEF core, and the stereoselective alkylation of a lactone. After the introduction of a glycine unit, the ABC ring system was stereoselectively constructed through intramolecular cycloaddition of the cyclic azomethine ylide.