title: Stereoselective Allylstannane Addition for a Convergent Synthesis of a Complex Molecule.
abstract: A convergent methodology with 13 lineal steps for the synthesis of phormidolides B and C macrocyclic core is described. Stereoselective formation of the tetrahydrofuran (THF) core was achieved using a stereocontrolled allylation reaction. The key step of the synthesis is a (Z)-1,5-anti stereoselective allylstannane addition where a new stereocenter and a trisubstituted double bond are formed simultaneously. Finally, Shiina macrolactonization conditions improved the yield of the final cyclization.
authors.affiliation: Institute for Research in Biomedicine, Barcelona Science Park-University of Barcelona , Baldiri Reixac 10, E-08028 Barcelona, Spain.
authors.forename: Alejandro
authors.initials: A
authors.lastname: Gil
authors.affiliation: Institute for Research in Biomedicine, Barcelona Science Park-University of Barcelona , Baldiri Reixac 10, E-08028 Barcelona, Spain.
authors.forename: Adriana
authors.initials: A
authors.lastname: Lorente
authors.affiliation: Institute for Research in Biomedicine, Barcelona Science Park-University of Barcelona , Baldiri Reixac 10, E-08028 Barcelona, Spain.
authors.forename: Fernando
authors.initials: F
authors.lastname: Albericio
authors.affiliation: Institute for Research in Biomedicine, Barcelona Science Park-University of Barcelona , Baldiri Reixac 10, E-08028 Barcelona, Spain.|Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona , 08028 Barcelona, Spain.
authors.forename: Mercedes
authors.initials: M
authors.lastname: Álvarez
mesh_terms: D003500:Cyclization; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008386:Marine Biology; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D018942:Macrolides; C475799:phormidolide; C000596130:phormidolide B; C000596129:phormidolide C