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  • Total synthesis of (-)-quinocarcin by gold(I)-catalyzed regioselective hydroamination.

Total synthesis of (-)-quinocarcin by gold(I)-catalyzed regioselective hydroamination.

Angewandte Chemie (International ed. in English) (2012-08-15)
Hiroaki Chiba, Shinya Oishi, Nobutaka Fujii, Hiroaki Ohno
ABSTRACT

In control: The novel and enantioselective total synthesis of (-)-quinocarcin includes the highly stereoselective preparation of the 2,5-cis-pyrrolidine by intramolecular amination, a selective substrate-controlled 6-endo-dig intramolecular alkyne hydroamination with a cationic Au(I) catalyst, and Lewis-acid-mediated ring-opening/halogenation sequence.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Pyrrolidine, ≥99.5%, purified by redistillation
Sigma-Aldrich
Pyrrolidine, ≥99.0%
Sigma-Aldrich
Pyrrolidine, 99%
Sigma-Aldrich
Pyrrolidine, FG