title: A diversity-oriented approach to indolocarbazoles via Fischer indolization and olefin metathesis: total synthesis of tjipanazole D and I.
abstract: New synthetic strategies to indolocarbazoles have been reported via two-fold Fischer indolization under green conditions using l-(+)-tartaric acid and N,N-dimethyl urea. Starting with cyclohexanone, a bench-top starting material, this methodology has been extended to the total synthesis of natural products such as tjipanazoles D and I as well as the core structure of asteropusazole and racemosin B. Here, atom economical reactions like ring-closing metathesis, enyne-metathesis, and the Diels-Alder reaction have been used as key steps. Diverse strategies demonstrated here are useful in medicinal chemistry and materials science to design a library of decorated indoles.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay Powai, Mumbai, 400 076, India. srk@chem.iitb.ac.in.
authors.forename: Sambasivarao
authors.initials: S
authors.lastname: Kotha
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay Powai, Mumbai, 400 076, India. srk@chem.iitb.ac.in.
authors.forename: Mohammad
authors.initials: M
authors.lastname: Saifuddin
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay Powai, Mumbai, 400 076, India. srk@chem.iitb.ac.in.
authors.forename: Vikas R
authors.initials: VR
authors.lastname: Aswar
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D007211:Indoles / Q000737:chemistry*
chemical_list: D000475:Alkenes; D002227:Carbazoles; D007211:Indoles; C096121:tjipanazole D; C000626196:tjipanazole I; C041514:carbazole