Concise catalytic asymmetric total syntheses of ancistrocladinium A and its atropdiastereomer. Issue 7 (18th April 2017)

• Record Type: Journal Article
• Authors: Kim, Kyung-Hee; Cheon, Cheol-Hong
• Is Part Of: Organic chemistry frontiers. Volume 4:Issue 7(2017)
• Page Start: 1341
• Page End: 1349
• Publication Date: 2017-04-18
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c7qo00195a
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : Asymmetric total syntheses of ancistrocladinium A and its atropdiastereomer were developed through stereospecific Bischler–Napieralski reaction of each of the tertiary amides with triflic anhydride. 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.