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1. Short Total Synthesis of (±)-γ-Lycorane by a Sequential Intramolecular Acylal Cyclisation (IAC) and Intramolecular Heck Addition Reaction.

Author

Monaco A, Szulc BR, Rao ZX, Barniol-Xicota M, Sehailia M, Borges BM, and Hilton ST

Subjects
Amaryllidaceae Alkaloids chemistry, Catalysis, Coordination Complexes chemistry, Cyclization, Lewis Acids chemistry, Palladium chemistry, Stereoisomerism, Amaryllidaceae Alkaloids chemical synthesis
Abstract

An intramolecular acylal cyclisation (IAC) approach to the synthesis of a range of bicyclic heterocycles is reported. As an example of the utility of the IAC reaction, the methodology was applied in a protecting-group-free five-step total synthesis of (±)-γ-lycorane, incorporating a new intramolecular Heck addition reaction to generate the pentacyclic core structure of the natural product in good yield., (© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Published
2017
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