Concise Total Synthesis of Tronocarpine
- 11 January 2021
- journal article
- research article
- Published by Wiley in Angewandte Chemie-International Edition
- Vol. 60 (2), 635-639
- https://doi.org/10.1002/anie.202009966
Abstract
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 alpha,beta-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.Keywords
Funding Information
- Takeda Science Foundation
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