title: Unified Approach to the Spiro(pyrrolidinyl-oxindole) and Hexahydropyrrolo[2,3-b]indole Alkaloids: Total Syntheses of Pseudophrynamines 270 and 272A.
abstract: The first enantioselective total syntheses of architecturally interesting prenylated pyrroloindole alkaloids, (-)-pseudophrynamines 272A (3d) and 270 (3b), have been achieved starting from enantioenriched 2-oxindoles having all-carbon quaternary stereocenters. A common strategy involving a thio-urea catalyzed aldol reaction is employed for the total synthesis of both spiro(pyrrolidinyl-oxindole) and hexahydropyrrolo[2,3-b]indole alkaloids.
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research Bhopal , Bhopal Bypass Road, Bhauri, Bhopal - 462 066, Madhya Pradesh, India.
authors.forename: Subhadip
authors.initials: S
authors.lastname: De
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research Bhopal , Bhopal Bypass Road, Bhauri, Bhopal - 462 066, Madhya Pradesh, India.
authors.forename: Mrinal Kanti
authors.initials: MK
authors.lastname: Das
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research Bhopal , Bhopal Bypass Road, Bhauri, Bhopal - 462 066, Madhya Pradesh, India.
authors.forename: Subhajit
authors.initials: S
authors.lastname: Bhunia
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research Bhopal , Bhopal Bypass Road, Bhauri, Bhopal - 462 066, Madhya Pradesh, India.
authors.forename: Alakesh
authors.initials: A
authors.lastname: Bisai
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry; D002384:Catalysis; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000078183:Oxindoles; D010830:Physostigmine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D054876:Prenylation; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000814:Aniline Compounds; D026121:Indole Alkaloids; D007211:Indoles; D000078183:Oxindoles; D013141:Spiro Compounds; C480174:coerulescine; C518152:esermethole; C443722:horsfiline; C000606782:pseudophrynamine 270; C000606783:pseudophrynamine 272A; C022960:2-oxindole; C092643:physovenine; C116609:3-hydroxybutanal; D010830:Physostigmine