General Strategy for the Synthesis of Antirhine Alkaloids: Divergent Total Syntheses of (+/-)-Antirhine, (+/-)-18,19-Dihydroantirhine, and Their 20-Epimers
- Title
- General Strategy for the Synthesis of Antirhine Alkaloids: Divergent Total Syntheses of (+/-)-Antirhine, (+/-)-18,19-Dihydroantirhine, and Their 20-Epimers
- Author
- 조천규
- Keywords
- INDOLE ALKALOIDS; STEREOSELECTIVE-SYNTHESIS; DL-18,19-DIHYDROANTIRHINE; (-)-ANTIRHINE; DERIVATIVES; SYNTHON
- Issue Date
- 2020-03
- Publisher
- AMER CHEMICAL SOC
- Citation
- ORGANIC LETTERS, v. 22, no. 6, page. 2354-2358
- Abstract
- A general synthetic strategy for antirhine alkaloids was developed in this study. The cyanide-catalyzed imino-Stetter reaction of ethyl 2-aminocinnamate and 4-bromopyridine-2-carboxaldehyde afforded the corresponding indole-3-acetic acid derivative. Subsequent formation of the six-membered C ring followed by trans-selective installation of the two-carbon unit at C-15 provided rapid access to the key intermediate. Stereoselective installation of substituents at C-20 allowed the total syntheses of (+/-)-antirhine, (+/-)-18,19-dihydroantirhine, and their 20-epimers, all of the known natural products in the antirhine family.
- URI
- https://pubs.acs.org/doi/10.1021/acs.orglett.0c00544https://repository.hanyang.ac.kr/handle/20.500.11754/162769
- ISSN
- 1523-7060; 1523-7052
- DOI
- 10.1021/acs.orglett.0c00544
- Appears in Collections:
- COLLEGE OF NATURAL SCIENCES[S](자연과학대학) > CHEMISTRY(화학과) > Articles
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