Deconstructive Asymmetric Total Synthesis of Morphine‐Family Alkaloid (−)‐Thebainone A
| Autor: | Adriana Y. Prichina, Si-Hua Hou, Guangbin Dong |
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| Rok vydání: | 2021 |
| Předmět: |
Steric effects
Natural product Molecular Structure Morphine 010405 organic chemistry Stereochemistry Alkaloid Enantioselective synthesis Total synthesis Substrate (chemistry) Stereoisomerism Ether General Medicine General Chemistry 010402 general chemistry 01 natural sciences Article Catalysis 0104 chemical sciences chemistry.chemical_compound Alkaloids chemistry Bond cleavage |
| Zdroj: | Angew Chem Int Ed Engl |
| ISSN: | 1521-3773 1433-7851 |
| DOI: | 10.1002/anie.202103553 |
| Popis: | Herein, we describe the development of a deconstructive strategy for the first asymmetric synthesis of (−)-thebainone A, capitalized on an enantioselective C−C bond activation and a C−O bond cleavage reaction. The Rh-catalyzed asymmetric ‘cut-and-sew’ transformation between sterically hindered trisubstituted alkenes and benzocyclobutenones allows efficient construction of the fused A/B/C rings and the all-carbon quaternary center of the natural product. The newly optimized conditions show a broad substrate scope and excellent enantioselectivity (up to 99.5:0.5 er). Taking advantage of the boron-mediated ether bond cleavage, synthesis of the morphine-alkaloid (−)-thebainone A has been completed with two complementary routes. |
| Databáze: | OpenAIRE |
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