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- Title
Bioinspired Total Synthesis of the Dimeric Indole Alkaloid (+)-Haplophytine by Direct Coupling and Late-Stage Oxidative Rearrangement.
- Authors
Satoh, Hitoshi; Ojima, Ken ‐ ichi; Ueda, Hirofumi; Tokuyama, Hidetoshi
- Abstract
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 AgNTf2-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.
- Subjects
DIMERIC ions; INDOLE alkaloid synthesis; DIAZABICYCLOOCTANE; ASPIDOSPERMA; COUPLING reactions (Chemistry); OXIDATIVE coupling
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 48, p15381
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201609285