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Concise Total Synthesis of Dihydrocorynanthenol, Protoemetinol, Protoemetine, 3-epi-Protoemetinol and Emetine
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2012 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 2, 398-408 p.Article 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, 398-408 p.
Keyword [en]
Organocatalysis, Asymmetric catalysis, Multicomponent reactions, Total synthesis, Natural products, Alkaloids
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-76751DOI: 10.1002/ejoc.201101296ISI: 000299295000023OAI: oai:DiVA.org:su-76751DiVA: diva2:527198
Funder
Swedish Research Council
Note

4

Available from: 2012-05-18 Created: 2012-05-16 Last updated: 2017-12-07Bibliographically approved

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