| Title: | "An efficient lactamisation/N-acyliminium Pictet-Spengler domino strategy for the diasteroselective synthesis of polyhydroxylated quinoxalinone, beta-carboline and quinazolinone derivatives" |
| Author(s): | Subba Reddy BV; Reddy BP; Reddy PV; Siriwardena A; |
| Address: | "Centre for Semiochemicals, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500 007, India. basireddy@iict.res.in. Centre for Semiochemicals, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500 007, India. basireddy@iict.res.in and Department of Chemistry, Yogi Vemana University, Kadapa, 516003, India. Department of Chemistry, Yogi Vemana University, Kadapa, 516003, India. Laboratoire de Glycochimie, des Antimicrobiens et des Agroressources, UMR 7378 CNRS, 33 rue Saint-Leu, 80039 Amiens, France. aloysius.siriwardena@u-picardie.fr" |
| ISSN/ISBN: | 1477-0539 (Electronic) 1477-0520 (Linking) |
| Abstract: | "A novel cascade strategy has been developed for the synthesis of polyhydroxylated tetrahydroindolo[1,2-a]pyrrolo[2,1-c]quinoxaline, tetrahydrodipyrrolo[1,2-a:2',1'-c]quinoxaline, hexahydro-1H-indolizino[8,7-b]indole, hexahydrobenzo[6,7]pyrrolo[1',2':1,2]azepino[3,4-b]indole, tetrahydrobenzo[4,5]imidazo[1,2-c]pyrrolo[1,2-a]quinazoline, and tetrahydropyrrolo[1,2-a]tetrazolo[1,5-c]quinazoline scaffolds. The key step is a lactamisation/Pictet-Spengler condensation of a bifunctional sugar-derived hydroxy-gamma-lactone component with an appropriate bifunctional aromatic amine component. This modular approach features the in situ-generation of a cyclic N-acyliminium intermediate that allows the diastereoselective assembly of these diverse polycyclic systems efficiently under mild and operationally simple conditions" |
| Notes: | "PubMed-not-MEDLINESubba Reddy, B V Reddy, B P Reddy, P V G Siriwardena, A eng England 2016/04/16 Org Biomol Chem. 2016 May 4; 14(18):4276-82. doi: 10.1039/c6ob00250a" |
