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Synthetic Studies towards Communesins: Diastereoselective Oxidative Rearrangement of Aurantioclavine Derivatives
Author(s) -
Suetsugu Satoshi,
Tsukano Chihiro,
Takemoto Yoshiji
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501194
Subject(s) - chemistry , stereocenter , aminal , epimer , stereoselectivity , stereochemistry , indole test , biomimetic synthesis , quaternary carbon , enantioselective synthesis , organic chemistry , catalysis
Communesins are a class of heptacyclic indole alkaloids that contain two aminal moieties and two contiguous quaternary carbon centers. We have investigated the construction of the pentacyclic skeleton of the communesins by employing the oxidative rearrangement of aurantioclavine derivatives, which are believed to be biosynthetic intermediates of the polycyclic communesin alkaloids. The quaternary C‐7 carbon center was constructed in a stereoselective manner, whereas the installation of the C‐11 stereocenter requires an epimerization process. The isolation of a 2‐ethoxyindolenine prior to the reduction of the nitro group and cyclization steps was critical to the success of this strategy.