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Bioinspired Total Synthesis of the Dimeric Indole Alkaloid (+)‐Haplophytine by Direct Coupling and Late‐Stage Oxidative Rearrangement
Author(s) -
Satoh Hitoshi,
Ojima Kenichi,
Ueda Hirofumi,
Tokuyama Hidetoshi
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201609285
Subject(s) - total synthesis , moiety , chemistry , nonane , aspidosperma , oxidative coupling of methane , indole test , stereochemistry , indole alkaloid , biomimetic synthesis , alkaloid , oxidative phosphorylation , organic chemistry , catalysis , biochemistry
A bioinspired convergent total synthesis of (+)‐haplophytine, a dimeric indole alkaloid with diazabicyclo[3.3.1]nonane and hexacyclic aspidosperma segments, is described. This synthesis involves the direct coupling of the two segments in a AgNTf 2 ‐mediated Friedel–Crafts reaction and construction of the diazabicyclo[3.3.1]nonane skeleton through late‐stage chemoselective aerobic oxidation of the 1,2‐diaminoethene moiety and a sequential semipinacol‐type rearrangement.