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Total Synthesis of Indole Alkaloid Alsmaphorazine D
Author(s) -
Zhu Chenlong,
Liu Zhaobo,
Chen Guanyu,
Zhang Kai,
Ding Hanfeng
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201409827
Subject(s) - chemistry , aminal , epimer , total synthesis , indole test , indole alkaloid , stereochemistry , intramolecular force , pyrrole , nonane , radical cyclization , enantioselective synthesis , biomimetic synthesis , catalysis , organic chemistry
A concise total synthesis of rac‐alsmaphorazine D has been described for the first time. The efficient synthetic strategy features four key transformations: 1) a catalytic intramolecular oxidative cyclization for the δ‐lactamindole backbone; 2) an oxidative cyclic aminal formation for the hexahydropyrrolo[2,3‐b]pyrrole framework; 3) a transannular radical cyclization for the construction of the diazabicyclo[3.3.1]nonane structure; and 4) a one‐pot desilylation/double epimerization reaction that affirms the relative stereochemistry.