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Enantioselective Total Synthesis and Absolute Configuration Assignment of (+)‐Tronocarpine Enabled by an Asymmetric Michael/Aldol Reaction.
- Source :
- Angewandte Chemie; 3/2/2020, Vol. 132 Issue 10, p3862-3867, 6p
- Publication Year :
- 2020
-
Abstract
- We present the first asymmetric total synthesis and absolute configuration determination of (+)‐tronocarpine. The [6.5.7.6.6] pentacyclic core was constructed at an early stage by using a sequential cyclization strategy through a newly developed catalytic asymmetric Michael/aldol cascade to build the aza[3.3.1]‐bridged cycle and a tandem reduction/hemiamidation procedure to assemble the seven‐membered lactam. The side‐chain functionalities were incorporated at a late stage by several appropriately orchestrated manipulations under mild conditions. The synthesis of enantiomerically pure (+)‐tronocarpine was achieved through a 20‐step longest linear sequence from tryptamine. [ABSTRACT FROM AUTHOR]
- Subjects :
- ALDOLS
ENANTIOMERIC purity
ASYMMETRIC synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 00448249
- Volume :
- 132
- Issue :
- 10
- Database :
- Complementary Index
- Journal :
- Angewandte Chemie
- Publication Type :
- Academic Journal
- Accession number :
- 141895122
- Full Text :
- https://doi.org/10.1002/ange.201914868