title: An allenic Pauson-Khand approach to 6,12-guaianolides.
abstract: Cyclocarbonylation of α-methylene butyrolactone-containing allene-ynes affords 6,12-guaianolide ring systems. Incorporation of the α-methylene butyrolactone early in a synthetic sequence is rare for reactivity reasons; however, this moiety proves to be beneficial to the allenic Pauson-Khand reaction. The three double bonds and the ketone in the resulting 5-7-5 ring system bear significant differences in their reactivity and are ideally positioned for synthetic application to 6,12-guaianolides and analogs.
authors: Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
authors: Francois
authors: F
authors: Grillet
authors: Chaofeng
authors: C
authors: Huang
authors: Kay M
authors: KM
authors: Brummond
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000737:chemistry*; D000466:Alkadienes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D045789:Sesquiterpenes, Guaiane / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000466:Alkadienes; D000480:Alkynes; D045789:Sesquiterpenes, Guaiane; D015107:4-Butyrolactone