title: Synthesis of β-Amino-Substituted Enones by Addition of Substituted Methyl Enones to Sulfinimines: Application to the Total Synthesis of Alkaloids (+)-Lasubine II and (+)-241D and the Formal Total Synthesis of (-)-Lasubine I.
abstract: Addition of silyl enol ethers obtained from substituted methyl enones to chiral sulfinimines afforded the β-amino-substituted enones with excellent selectivity. Utility of the obtained N-sulfinyl β-amino ketones possessing α,β-unsaturation is exemplified in the total synthesis of the quinolizidine alkaloid natural products (-)-lasubine I, (+)-lasubine II, and substituted piperidine alkaloid (+)-241-D.
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science , Bangalore 560012, India.
authors.forename: Arava Amaranadha
authors.initials: AA
authors.lastname: Reddy
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science , Bangalore 560012, India.
authors.forename: Polimera Obula
authors.initials: PO
authors.lastname: Reddy
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science , Bangalore 560012, India.
authors.forename: Kavirayani R
authors.initials: KR
authors.lastname: Prasad
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D007097:Imines / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D013058:Mass Spectrometry; D015394:Molecular Structure; D066244:Proton Magnetic Resonance Spectroscopy; D011807:Quinolizines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D007097:Imines; D007211:Indoles; D007659:Ketones; D011807:Quinolizines; D013452:Sulfonium Compounds; C414385:lasubin I; C522016:sulfinimine