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Concise Total Synthesis of Dihydrocorynanthenol, Protoemetinol, Protoemetine, 3-epi-Protoemetinol and Emetine
Stockholm Univ, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden .
Stockholm Univ, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden .
Stockholm Univ, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden .
Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design. (Armando Córdova)
2012 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 2, p. 398-408Article in journal (Refereed) Published
Abstract [en]

A concise asymmetric assembly of secologanine tryptamine and dopamine alkaloids by means of a one-pot three-component cascade reaction methodology is disclosed. This is demonstrated by the expeditious total syntheses of (-)-dihydrocorynanthenol, (-)-protoemetinol, (-)-protoemetine, (-)-3-epi-protoemetinol, and emetine (3-6 steps). The biomimetic synthetic strategy involved the following key steps: (i) One-pot three-component highly enantioselective catalytic Michael/Pictet-Spengler/lactamization cascade reactions; (ii) One-pot tandem Swern oxidation/Wittig sequences; (iii) One-pot tandem hydrogenation sequences.

Place, publisher, year, edition, pages
2012. no 2, p. 398-408
Keyword [en]
Organocatalysis; Asymmetric catalysis; Multicomponent reactions; Total synthesis; Natural products; Alkaloids
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:miun:diva-15961DOI: 10.1002/ejoc.201101296ISI: 000299295000023Scopus ID: 2-s2.0-84855185340OAI: oai:DiVA.org:miun-15961DiVA, id: diva2:505800
Available from: 2012-02-25 Created: 2012-02-25 Last updated: 2017-12-07Bibliographically approved

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