A Three‐Step Synthesis of the Guaianolide Ring System. Issue 15 (11th April 2014)

• Record Type: Journal Article
• Authors: Hullaert, Jan; Laplace, Duchan R.; Winne, Johan M.
• Is Part Of: European journal of organic chemistry. Issue 15(2014)
• Page Start: 3097
• Page End: 3100
• Publication Date: 2014-04-11
• Subjects: Total synthesis -- Natural products -- Terpenoids -- Cycloaddition -- Oxygen heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402170
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: By using a gallium(III) triflate catalyzed intramolecular (4+3) cycloaddition, a few functionalized furan‐derived tricycles that share the common guaianolide sesquiterpene ring system were prepared in a stereoselective manner in only three steps from commercially available starting materials. A discussion of the formation of alternative products is included, with possible substrate requirements to achieve the key cycloaddition step in an efficient way. Abstract : The guaianolide ring system, a naturally abundant tricyclic sesquiterpenoid scaffold, is assembled in just three straightforward synthetic operations by using a highly diastereoselective intramolecular (4+3) cycloaddition reaction of a catalytically generated furfuryl cation intermediate.