title: Diversity oriented convergent access for collective total synthesis of bioactive multifunctional carbazole alkaloids: synthesis of carbazomycin A, carbazomycin B, hyellazole, chlorohyellazole, and clausenaline D.
abstract: Facile syntheses of imperative carbazole alkaloids carbazomycin A, carbazomycin B, hyellazole, chlorohyellazole, and clausenaline D have been demonstrated starting from readily available Boc-protected 3-formylindole and dimethyl maleate. The suitably substituted aromatic rings have been designed comprising three/four significant C-C bond forming reactions. The competent Wittig reaction, selective monoalkylations, one-pot regioselective Weinreb amide formation and Boc-deprotection, well designed Grignard reactions, dehydrative intramolecular cyclizations, and Baeyer-Villiger rearrangement of aromatic aldehydes were the main features.
authors.affiliation: Division of Organic Chemistry, National Chemical Laboratory (CSIR) , Pune 411 008, India.
authors.forename: Shivaji B
authors.initials: SB
authors.lastname: Markad
authors.forename: Narshinha P
authors.initials: NP
authors.lastname: Argade
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000737:chemistry; D008298:Maleates / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: C528934:3-formylindole; D000447:Aldehydes; D002227:Carbazoles; D026121:Indole Alkaloids; D007211:Indoles; D008298:Maleates; C000599396:chlorohyellazole; C000599397:clausenaline D; C000599395:hyellazole; C041514:carbazole; C026754:carbazomycin B; C026753:carbazomycin A; C004780:dimethyl maleate