title: Phormidolides B and C, cytotoxic agents from the sea: enantioselective synthesis of the macrocyclic core.
abstract: New cytotoxic polyketide macrolides named phormidolides B and C were isolated from a marine sponge of the Petrosiidae family collected off the coast of Pemba (Tanzania). The isolation, structure elucidation, and enantioselective synthesis of three diastereomers of the macrocyclic core is described herein. The described synthetic methodology started from 2-deoxy-D-ribose or 2-deoxy-L-ribose and afforded the desired macrocycles with high enantiomeric purity. The key step of the synthesis is the formation of the Z-trisubstituted double bond using a Julia-Kocienski olefination. The versatility of the synthetic methodology may provide access to other enantiopure macrocycles by making changes in the starting materials or chiral inductors.
authors.affiliation: Institute for Research in Biomedicine, Barcelona Science Park-University of Barcelona, Baldiri i Reixac 10, 08028 Barcelona (Spain); CIBER-BBN, Networking Centre on Bioengineering Biomaterials and Nanomedicine, 08028 Barcelona (Spain) http://www.pcb.ub.edu/fama/htm/home.htm.
authors.forename: Adriana
authors.initials: A
authors.lastname: Lorente
authors.forename: Alejandro
authors.initials: A
authors.lastname: Gil
authors.forename: Rogelio
authors.initials: R
authors.lastname: Fernández
authors.forename: Carmen
authors.initials: C
authors.lastname: Cuevas
authors.forename: Fernando
authors.initials: F
authors.lastname: Albericio
authors.forename: Mercedes
authors.initials: M
authors.lastname: Álvarez
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D019073:HT29 Cells; D006801:Humans; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D010084:Oxidation-Reduction; D011161:Porifera; D013237:Stereoisomerism
chemical_list: D018942:Macrolides; C000596130:phormidolide B; C000596129:phormidolide C
keywords: anticancer agents; enantioselectivity; natural products; polyketides; total synthesis