Total Synthesis of (-)-Secu'amamine A Exploiting Type II Anion Relay Chemistry.
A total synthesis of (-)-secu'amamine A has been achieved exploiting Type II Anion Relay Chemistry (ARC) to provide the full linear carbon and nitrogen skeleton in a single flask with the requisite stereochemistry and functionality. A mechanistic rationale is also proposed to account for the stereochemical outcome of the key aldol reaction leading to the advanced aza tricyclic core.
Department of Chemistry, Laboratory for Research on the Structure of Matter and Monell Chemical Senses Center, University of Pennsylvania , Philadelphia, Pennsylvania 19104, United States.
Heeoon
H
Han
Department of Chemistry, Laboratory for Research on the Structure of Matter and Monell Chemical Senses Center, University of Pennsylvania , Philadelphia, Pennsylvania 19104, United States.
Amos B
AB
Smith
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D019665:Euphorbiaceae / Q000737:chemistry; D006572:Heterocyclic Compounds, Bridged-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D006572:Heterocyclic Compounds, Bridged-Ring; C519982:secu'amamine A