Enantioselective Construction of Cyclic Quaternary Centers: (−)-Mesembrine
- 6 December 2000
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 66 (1), 143-147
- https://doi.org/10.1021/jo001237g
Abstract
The preparation of the crystalline amide 2 is reported. Conjugate addition to 2 proceeded with the expected high diastereocontrol to give 3. This set the stage for subsequent intramolecular alkylidene C−H insertion to give, after ozonolysis and aldol condensation, (−)-mesembrine 1. Amide 2 should be a useful chiron for the enantioselective construction of cyclic quaternary centers.Keywords
This publication has 16 references indexed in Scilit:
- Cyclohexenone Construction by Intramolecular Alkylidene C−H Insertion: Synthesis of (+)-CassiolThe Journal of Organic Chemistry, 1996
- Efficient Intramolecular C-H Insertion by an Alkylidene Carbene Generated from a Vinyl ChlorideThe Journal of Organic Chemistry, 1995
- Stereoselective total synthesis of topographically constrained designer amino acids: 2′, 6′-dimethyl-β-methyltyrosinesTetrahedron, 1995
- Asymmetric 1,4-addition of organocuprates to chiral .alpha.,.beta.-unsaturated N-acyl-4-phenyl-2-oxazolidinones: a new approach to the synthesis of chiral .beta.-branched carboxylic acidsThe Journal of Organic Chemistry, 1993
- Alkylidenecarbenes from 1-diazo-1-alkenes: their electrophilicity and stereochemistry of [2 + 2]-cycloadditionThe Journal of Organic Chemistry, 1992
- Reactions of alkylidenecarbenes derived from N,N-disubstituted-2-oxopropanamides: the formation of 3-pyrrol-2-ones and 2-butynamidesThe Journal of Organic Chemistry, 1986
- Cyclisation of allyl silanes. Formal total synthesis of (±)-mesembrineTetrahedron Letters, 1985
- Enantiocontrolled synthesis of quaternary carbon centers. 3,3-Disubstituted cyclopentanones. (+)-α-cuparenone.Tetrahedron Letters, 1984
- Enantioselective aldol condensations. 2. Erythro-selective chiral aldol condensations via boron enolatesJournal of the American Chemical Society, 1981
- Enantioselective synthesis of natural mesembrine using (D)-mannitol as a chiral template, a model study for the enantioselective synthesis of the amaryllidaceae alkaloidsTetrahedron Letters, 1981