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Concise Total Synthesis of Tronocarpine
Author(s) -
Nakayama Atsushi,
Nakamura Tenta,
Zaima Toshihiro,
Fujimoto Saho,
Karanjit Sangita,
Namba Kosuke
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202009966
Subject(s) - total synthesis , stereocenter , chemistry , nonane , stereochemistry , indole test , tandem , aldol reaction , aldehyde , cascade reaction , azide , intramolecular force , enantioselective synthesis , organic chemistry , catalysis , materials science , composite material
A concise total synthesis of tronocarpine, a chippiine‐type indole alkaloid, was accomplished. The key feature of this total synthesis is a one‐pot construction of the pentacyclic skeleton containing an azabicyclo[3.3.1]nonane core by tandem cyclization from an indole derivative with all carbon side chains and functional groups. This tandem cyclization consists of α,β‐unsaturated aldehyde formation, intramolecular aldol reaction, six‐membered lactamization, azide reduction, and seven‐membered lactamization. The stereochemical outcome in this tandem cyclization is controlled by the stereocenter at the C14 position. This strategy can be utilized to synthesize other chippiine‐type alkaloids with azabicyclo[3.3.1]nonane skeletons.