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Concise catalytic asymmetric total syntheses of ancistrocladinium A and its atropdiastereomer
- Authors
- Kim, Kyung-Hee; Cheon, Cheol-Hong
- Issue Date
- 1-7월-2017
- Publisher
- ROYAL SOC CHEMISTRY
- Citation
- ORGANIC CHEMISTRY FRONTIERS, v.4, no.7, pp.1341 - 1349
- Indexed
- SCIE
SCOPUS
- Journal Title
- ORGANIC CHEMISTRY FRONTIERS
- Volume
- 4
- Number
- 7
- Start Page
- 1341
- End Page
- 1349
- ISSN
- 2052-4110
- Abstract
- Asymmetric total syntheses of ancistrocladinium A and its atropdiastereomer, in an atropisomerically pure form, are described. Chiral phosphoric acid-catalyzed asymmetric reductive amination of 1-aryl propanone and naphthylamine followed by acetylation provided two atropisomerically pure tertiary amides. Subsequent stereospecific Bischler-Napieralski reaction of each of these tertiary amides with triflic anhydride provided ancistrocladinium A or its atropdiastereomer, as a single atropisomer, respectively.
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