IMDA-Radical Cyclization Approach to (+)-Himbacine
- 9 September 2003
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (20) , 3603-3606
- https://doi.org/10.1021/ol0353058
Abstract
[reaction: see text] A formal total synthesis of the selective muscarinic receptor antagonist himbacine is presented. Key C-C bond-forming steps include an intramolecular Diels-Alder reaction, Stille coupling reactions, and a 6-exo-trig acyl radical cyclization to a conjugated enyne. An unexpected secondary alcohol to chloride conversion is witnessed during attempted thionocarbonate formation.Keywords
This publication has 17 references indexed in Scilit:
- First Synthesis of the Dendralene Family of Fundamental HydrocarbonsPublished by Wiley ,2000
- A novel total synthesis of (+)-himbacine, a potent antagonist of the muscarinic receptor of M2 subtypeTetrahedron Letters, 1999
- A Highly Efficient Total Synthesis of (+)-HimbacineJournal of the American Chemical Society, 1996
- Studies directed towards the total synthesis of (±)-himbacineTetrahedron Letters, 1995
- Alzheimer's therapy: an approach to novel muscarinic ligands based upon the naturally occurring alkaloid himbacine.Bioorganic & Medicinal Chemistry Letters, 1992
- Structure-activity relationships of some Galbulimima alkaloids related to himbacineEuropean Journal of Pharmacology, 1990
- A useful method for converting 2° alcohols to their chlorides with retention of configurationTetrahedron Letters, 1988
- A general strategy for elaboration of the dithiocarbonyl functionality, -(C:O)SS-: application to the synthesis of bis(chlorocarbonyl)disulfane and related derivatives of thiocarbonic acidsThe Journal of Organic Chemistry, 1983
- Bent bonds in the bridgehead triptycyl radicalJournal of the American Chemical Society, 1977
- The Nature of Chromium(VI) in Acid Solution and Its Relation to Alcohol OxidationJournal of the American Chemical Society, 1964