title: First total synthesis of (+)-apotrisporin E and (+)-apotrientriols A-B: a cyclization approach to apocarotenoids.
abstract: The first total synthesis of the natural apocarotenoids (+)-apotrisporin E (1) and (+)-apotrientriols A and B (2-3) has been accomplished. The structure, relative stereochemistry and the assignation of the absolute configuration have been confirmed. This is a fast and easy access to this family of natural products whose key steps are a diastereoselective cyclization and a HWE olefination to attach the dienic side chain. This work also opens the door to the synthesis of other apocarotenoids such as trisporols and trisporic acids.
authors.affiliation: Department of Organic Chemistry, and Institute of Biotechnology, University of Granada, Avda Fuentenueva, 18071 Granada, Spain.
authors.forename: José A
authors.initials: JA
authors.lastname: González-Delgado
authors.forename: Jesús F
authors.initials: JF
authors.lastname: Arteaga
authors.forename: M Mar
authors.initials: MM
authors.lastname: Herrador
authors.forename: Alejandro F
authors.initials: AF
authors.lastname: Barrero
mesh_terms: D002338:Carotenoids / Q000737:chemistry*; D003500:Cyclization; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry; D006018:Glycols / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D003512:Cyclohexanones; D006018:Glycols; D002338:Carotenoids