Divergent synthetic route to new cyclopenta[c]pyran iridoids: syntheses of jatamanin A, F, G and J, gastrolactone and nepetalactone. Issue 4 (8th December 2015)

• Record Type: Journal Article
• Authors: Sim, Jaehoon; Yoon, Inah; Yun, Hwayoung; An, Hongchan; Suh, Young-Ger
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 4(2016)
• Page Start: 1244
• Page End: 1251
• Publication Date: 2015-12-08
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c5ob02147b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Six natural iridoids including jatamanin A, F, G and J, gastrolactone and nepetalactone have been synthesized via the efficient transformation of a core cyclopenta[ c ]pyran intermediate. Abstract : Six natural iridoids including jatamanin A, F, G and J, gastrolactone and nepetalactone have been synthesized via the efficient transformation of a core cyclopenta[ c ]pyran intermediate. Key features of the syntheses include the stereoselective construction of the core cyclopenta[ c ]pyran skeleton of the iridoid lactones via a Pd(0)-catalyzed intramolecular allylic alkylation, and the facile transformation of the common intermediate into natural iridoids.