Concise catalytic asymmetric total syntheses of ancistrocladinium A and its atropdiastereomer

Kyung Hee Kim, Cheol-Hong Cheon

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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.

Original languageEnglish
Pages (from-to)1341-1349
Number of pages9
JournalOrganic Chemistry Frontiers
Volume4
Issue number7
DOIs
Publication statusPublished - 2017 Jul 1

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Amides
Amination
Acetylation
ancistrocladinium A
phosphoric acid
triflic anhydride

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Concise catalytic asymmetric total syntheses of ancistrocladinium A and its atropdiastereomer. / Kim, Kyung Hee; Cheon, Cheol-Hong.

In: Organic Chemistry Frontiers, Vol. 4, No. 7, 01.07.2017, p. 1341-1349.

Research output: Contribution to journalArticle

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