General Strategy for the Synthesis of Antirhine Alkaloids: Divergent Total Syntheses of (+/-)-Antirhine, (+/-)-18,19-Dihydroantirhine, and Their 20-Epimers
- Authors
- Bae, Cheolwoo; Park, Eunjoon; Cho, Cheon-Gyu; Cheon, Cheol-Hong
- Issue Date
- Mar-2020
- Publisher
- AMER CHEMICAL SOC
- Citation
- ORGANIC LETTERS, v.22, no.6, pp.2354 - 2358
- Indexed
- SCIE
SCOPUS
- Journal Title
- ORGANIC LETTERS
- Volume
- 22
- Number
- 6
- Start Page
- 2354
- End Page
- 2358
- URI
- https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/146112
- DOI
- 10.1021/acs.orglett.0c00544
- ISSN
- 1523-7060
- 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.
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