A De Novo Approach for the Stereoselective Synthesis of Cyclopenta[c]pyranone Scaffold Present in Iridoids: Formal Syntheses of Isoboonein, Iridomyrmecin and Isoiridomyrmecin. Issue 20 (28th May 2018)

• Record Type: Journal Article
• Authors: Kaurav, Manvendra Singh; Kumar, Virendra; Kumar, Dileep; Khan, Tabrez
• Is Part Of: ChemistrySelect. Volume 3:Issue 20(2018)
• Page Start: 5566
• Page End: 5570
• Publication Date: 2018-05-28
• Subjects: cyclopenta[c]pyranone -- intramolecular Pauson-Khand reaction -- iridoids -- stereoselectivity -- natural products; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201800421
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A conceptually new intramolecular Pauson‐Khand reaction (IPKR) based general strategy has been demonstrated for the formal syntheses of isoboonein, iridomyrmecin and isoiridomyrmecin from very cheap, commercially available starting material. Abstract : A new and efficient racemic route employing an intramolecular Pauson‐Khand reaction as the key step for stereoselective construction of the cyclopenta[c]pyran‐3‐one scaffold present in iridoid class of natural products is described, starting from a very cheap, commercially available starting material. Further, the scope of approach for the formal syntheses of isoboonein, iridomyrmecin and isoiridomyrmecin has been demonstrated.