An Approach to the Skeleton of the Securinega Alkaloids. The Total Synthesis of (±)-Securinine
- 6 February 2001
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (5) , 703-706
- https://doi.org/10.1021/ol0070482
Abstract
[structure: see text]. The concise total synthesis of securinine in nine steps from readily available starting materials is described. Key steps of the synthesis include an addition of a silyloxyfuran to an in situ generated iminium ion and a novel ring closing metathesis reaction.Keywords
This publication has 17 references indexed in Scilit:
- A novel intramolecular Diels–Alder approach to securinega alkaloids: formal synthesis of securinineTetrahedron Letters, 2000
- The Vinylogous Aldol Reaction: A Valuable, Yet Understated Carbon−Carbon Bond-Forming ManeuverChemical Reviews, 2000
- The stereochemical course of intramolecular vinylogous Mannich reactionsTetrahedron Letters, 1997
- Trimethylsilyl Trifluoromethanesul Fonate (Tmsotf) Catalyzed Amidoalkylation of Silylenolethers. Stereocontrolled Syntheses of (+/-)-Sedamine and (+/-)-NorsedamineSynthetic Communications, 1991
- Synthesis of 1-Hydroxy-7-azatricyclo[6.3.1.02.7]dodecan-9-ones: Potential Intermediates for the Total Synthesis of SecurininesHETEROCYCLES, 1989
- Securinine alkaloids: A new class of GABA receptor antagonistBrain Research, 1985
- The total synthesis of securinine and virosecurinineTetrahedron, 1967
- The Crystal Structure of Securinine Hydrobromide Dihydrate and the Molecular Structure of SecurinineCHEMICAL & PHARMACEUTICAL BULLETIN, 1965
- Studies on the alkaloids of Securinega virosa Pax. et Hoffm.—ITetrahedron, 1963
- Studies on securinine and allosecurinineTetrahedron Letters, 1962