Bioinspired Total Synthesis of the Dimeric Indole Alkaloid (+)‐Haplophytine by Direct Coupling and Late‐Stage Oxidative Rearrangement | Zendy

Satoh Hitoshi | Zendy; Ojima Kenichi | Zendy; Ueda Hirofumi | Zendy; Tokuyama Hidetoshi | Zendy

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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.

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