title: Chemoenzymatic synthesis of trans-tetrahydrofuran cores of annonaceous acetogenins from bromobenzene.
abstract: Two types of trans-THF cores, present in acetogenins, have been synthesized by an intramolecular iodoetherification reaction. The starting alkenol was obtained in a few steps from a chiral cis-diol resulting from microbial oxidation of bromobenzene. The cyclization gave complete stereoselectivity for trans-THF cores with either (S,S) or (R,R) configurations at the THF chiral carbons.
authors.affiliation: Departamento de Química Orgánica, Facultad de Química, Universidad de la República, C.C. 1157 Montevideo, Uruguay.
authors.forename: Juan Carlos
authors.initials: JC
authors.lastname: Ramos
authors.forename: Margarita
authors.initials: M
authors.lastname: Brovetto
authors.forename: Gustavo A
authors.initials: GA
authors.lastname: Seoane
mesh_terms: D054378:Acetogenins / Q000138:chemical synthesis* / Q000737:chemistry; D000438:Alcohols / Q000737:chemistry; D029061:Annonaceae / Q000737:chemistry; D001969:Bromobenzenes / Q000737:chemistry*; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D054378:Acetogenins; D000438:Alcohols; D001969:Bromobenzenes; D005663:Furans; C018674:tetrahydrofuran