Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 2, Pages 635-639Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202009966
Keywords
alkaloids; equilibrium; natural products; tandem cyclization; total synthesis
Categories
Funding
- JSPS KAKENHI [20K09396, JP19H02851, JP16H01156]
- Uehara Memorial Foundation
- Takeda Science Foundation
- Tokushima University [1802001]
- Grants-in-Aid for Scientific Research [20K09396] Funding Source: KAKEN
Ask authors/readers for more resources
The concise total synthesis of tronocarpine, a chippiine-type indole alkaloid, was achieved through a one-pot construction of a pentacyclic skeleton. This strategy, controlled by the stereocenter at the C14 position, can be used to synthesize other chippiine-type alkaloids with azabicyclo[3.3.1]nonane skeletons.
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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available