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Total Synthesis of (−)‐Alstofolinine A through a Furan Oxidation/Rearrangement and Indole Nucleophilic Cyclization Cascade
Author(s) -
Zhang Lei,
Zhang Ye,
Li Wenting,
Qi Xiangbing
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201900156
Subject(s) - indole test , chemistry , nonane , furan , nucleophile , total synthesis , cascade , combinatorial chemistry , cascade reaction , stereochemistry , organic chemistry , catalysis , chromatography
Abstract A reaction cascade of aza‐Achmatowicz rearrangement followed by indole nucleophilic cyclization was developed to generate the common indole‐fused azabicyclo[3.3.1]nonane core of the macroline family alkaloids. The key to the success of the strategy relies on the careful manipulation of protecting groups and judicious selection of chemoselective furan oxidation conditions. The synthetic utility was further demonstrated on the asymmetric total synthesis of (−)‐alstofolinine A.