title: Iron(III) catalyzed direct synthesis of cis-2,7-disubstituted oxepanes. The shortest total synthesis of (+)-isolaurepan.
abstract: Prins cyclization of bis-homoallylic alcohols with aldehydes catalyzed by iron(III) salts shows excellent cis selectivity and yields to form 2,7-disubstituted oxepanes. The iron(III) is able to catalyze this process with unactivated olefins. This cyclization was used as the key step in the shortest total synthesis of (+)-isolaurepan.
authors.affiliation: Instituto Universitario de Bio-Orgánica Antonio González, Departamento de Química Orgánica, Universidad de La Laguna, C/Astrofísico Francisco Sánchez 2, 38206 La Laguna, Tenerife, Spain.
authors.forename: Martín A
authors.initials: MA
authors.lastname: Purino
authors.forename: Miguel A
authors.initials: MA
authors.lastname: Ramírez
authors.forename: Antonio H
authors.initials: AH
authors.lastname: Daranas
authors.forename: Víctor S
authors.initials: VS
authors.lastname: Martín
authors.forename: Juan I
authors.initials: JI
authors.lastname: Padrón
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D058085:Iron Compounds / Q000737:chemistry*; D044722:Laurencia / Q000737:chemistry; D015394:Molecular Structure; D010082:Oxepins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000447:Aldehydes; D000475:Alkenes; D058085:Iron Compounds; D010082:Oxepins; C578360:isolaurepan