title: Total synthesis of neuroprotectin D1 analogues derived from omega-6 docosapentaenoic acid (DPA) and adrenic acid (AdA) from a common pivotal, late-stage intermediate.
abstract: The first total synthesis of three omega-6 dihydroxylated (E,E,Z)-docosatrienes has been successfully achieved employing a flexible strategy. The key features encompass a Boland semireduction, to create the (E,E,Z)-triene via an (E,E)-ynediene, and a selective deprotection of a tris(tert-butyldimethylsilyl) ether. The main advantage of the present strategy over previous syntheses of noncyclic dihydroxylated PUFA metabolites derived from docosahexaenoic and arachidonic acids comes from the introduction of the polar head chain at the very end of the synthesis from an advanced, pivotal aldehyde. In terms of divergency this enables late-stage modification of the head group.
authors.affiliation: Faculté de Pharmacie, Institut des Biomolécules Max Mousseron (IBMM, UMR5247 CNRS-UM1-UM2-ENSCM) , 15 av. C. Flahault, BP 14491, 34093 Montpellier Cedex 5, France.
authors.forename: Gandrath
authors.initials: G
authors.lastname: Dayaker
authors.forename: Thierry
authors.initials: T
authors.lastname: Durand
authors.forename: Laurence
authors.initials: L
authors.lastname: Balas
mesh_terms: D001095:Arachidonic Acids / Q000737:chemistry*; D004281:Docosahexaenoic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D005231:Fatty Acids, Unsaturated / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001095:Arachidonic Acids; D005231:Fatty Acids, Unsaturated; C487679:protectin D1; C011395:adrenic acid; D004281:Docosahexaenoic Acids; C026219:docosapentaenoic acid