Addition of Metallo Enolates to Chiral 1-Acylpyridinium Salts: Total Synthesis of (+)-Cannabisativine
- 15 February 2000
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (6) , 855-857
- https://doi.org/10.1021/ol0056271
Abstract
A novel route to the first asymmetric synthesis of (+)-cannabisativine (1) is described. The total synthesis of 1 was accomplished with a high degree of regio- and stereoselectivity in 19 steps and 9% overall yield.Keywords
This publication has 16 references indexed in Scilit:
- The Mukaiyama-Michael Reaction of N-Acyl-2,3-dihydro-4-pyridones: Regio- and Stereoselective Synthesis of cis-2,6-Disubstituted 1,2,5,6-TetrahydropyridinesOrganic Letters, 1999
- Efficient method for preparation of N-methoxy-N-methyl amides by reaction of lactones or esters with Me2AlClMeONHMe·HClTetrahedron Letters, 1997
- Asymmetric Synthesis of 2-Alkyl(Aryl)-2,3-dihydro-4-pyridones by Addition of Grignard Reagents to Chiral 1-Acyl-4-methoxypyridinium SaltsJournal of the American Chemical Society, 1994
- The Structure and Function of Estrogens. IX. Synthesis of the trans Isomer of 5,5,10b-Trimethyl-4b,5,6,10b,11,12-hexahydrochrysene-2,8-diolAustralian Journal of Chemistry, 1988
- A total synthesis of (±)-cannabisativineTetrahedron Letters, 1985
- Total synthesis of anhydrocannabisativeneJournal of the American Chemical Society, 1984
- Total synthesis of (±)-cannabisativineTetrahedron Letters, 1984
- Benzyl trichloroacetimidate, a versatile reagent for acid-catalysed benzylation of hydroxy-groupsJournal of the Chemical Society, Chemical Communications, 1981
- Isolation of Cannabisativine, an Alkaloid, from Cannabis sativa L. RootJournal of Pharmaceutical Sciences, 1976
- A New Method for the Preparation of 3-Substituted-2-oxazolidonesJournal of the American Chemical Society, 1955