title: A regioselective facile synthesis of furo[3,4-b]carbazolones: application to the total synthesis of mafaicheenamine E and claulansine D.
abstract: 1-Hydroxycarbazole-2,3-dicarboxylates have been shown to undergo chemoselective reductive cyclization to furo[3,4-b]carbazolones on reaction with LiAlH4. One of the furocarbazolones is utilized to accomplish the first total synthesis of claulansine D and mafaicheenamine E in 9 and 6 steps respectively. The other key steps of the syntheses are addition of an allylic indium reagent and CC double bond isomerization.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, India. dmal@chem.iitkgp.ernet.in.
authors.forename: Dipakranjan
authors.initials: D
authors.lastname: Mal
authors.forename: Joyeeta
authors.initials: J
authors.lastname: Roy
mesh_terms: D017607:Aluminum Compounds / Q000737:chemistry; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D018020:Lithium Compounds / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D017607:Aluminum Compounds; D002227:Carbazoles; D002264:Carboxylic Acids; D007783:Lactones; D018020:Lithium Compounds; C042073:lithium aluminum hydride