Highly Enantioselective Approach to Indolizidines: Preparation of (+)-(1S,8aS)-1-Hydroxyindolizidine and (−)-Slaframine
- 19 September 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (21), 6966-6972
- https://doi.org/10.1021/jo0005621
Abstract
A highly stereoselective approach to (-)-slaframine and its probable biosynthetic precursor (+)-(1S,8aS)-1-hydroxyindolizidine has been developed based on a diastereofacially selective cycloaddition of dichloroketene with a chiral dienol ether.Keywords
This publication has 17 references indexed in Scilit:
- Formal Total Synthesis of Enantiopure (−)-Anisomycin, Antibiotic from StreptomycesThe Journal of Organic Chemistry, 1999
- Novel Enantioselective Approach to γ-Lactams from Chiral Enol Ethers: Synthesis of (−)-StatineThe Journal of Organic Chemistry, 1996
- Chiral Enol Ethers in Asymmetric Synthesis: Preparation of the .beta.-Oxygenated Lactones (-)-Blastmycinolactol, (+)-Blastmycinone, (-)-NFX-2, and (+)-AntimycinoneThe Journal of Organic Chemistry, 1995
- Novel, enantioselective lactone construction. First synthesis of methylenolactocin, antitumor antibiotic from Penicillium spThe Journal of Organic Chemistry, 1992
- Enantioselective ring construction through asymmetric olefin-ketene cycloaddition. A highly enantiocontrolled approach to (-)-.alpha.-cuparenone and (+)-.beta.-cuparenoneJournal of the American Chemical Society, 1987
- The Indolizidine Alkaloids, Slaframine and Swainsonine: Contaminants in Animal ForagesAnnual Review of Nutrition, 1985
- A synthesis of (.+-.)-lineatin by 2 + 2 cycloaddition of dichloroketene with a cyclic allyl etherThe Journal of Organic Chemistry, 1985
- Synthesis of 2-substituted 4-oxahomoadamantanesThe Journal of Organic Chemistry, 1978
- Organic sulfur chemistry. Part XXII. The reaction of sulfinate esters with Grignard and organocopper lithium reagents. A useful route to chiral sulfoxidesThe Journal of Organic Chemistry, 1976
- Structure of the fluorescent Y base from yeast phenylalanine transfer ribonucleic acidJournal of the American Chemical Society, 1970