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Published on: August 12, 2019
Concise Total Synthesis of Tronocarpine
Atsushi Nakayama1, Tenta Nakamura1, Toshihiro Zaima1
1Graduate School of Pharmaceutical Sciences, Tokushima University, 1-78 Shomachi, Tokushima, Tokushima, 770-8505, Japan.
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 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.
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