title: Synthesis of (E)-4-Bromo-3-methoxybut-3-en-2-one, the Key Fragment in the Polyhydroxylated Chain Common to Oscillariolide and Phormidolides A-C.
abstract: The terminal bromomethoxydiene (BMD) moiety of the polyhydroxylated chain present in phormidolides and oscillariolides has been synthesized for first time. Several strategies for the stereoselective synthesis of the 4-bromo-3-methoxybut-3-en-2-ones are described. Furthermore, a preliminary study to successfully introduce the BMD within the polyol chain and the fatty acid allowed us to corroborate the end structure of the polyol.
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.
authors.forename: Alejandro
authors.initials: A
authors.lastname: Gil
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.
authors.forename: Janire
authors.initials: J
authors.lastname: Lamariano-Merketegi
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.|University of Zurich, Winterthurerstrasse 190, 8057, Zürich, Switzerland.
authors.forename: Adriana
authors.initials: A
authors.lastname: Lorente
authors.affiliation: CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, 08028, Barcelona, Spain.|Department of Organic Chemistry, University of Barcelona, 08028, Barcelona, Spain.|School of Chemistry, University of Kwa-Zulu-Natal, 4001, Durban, South Africa.
authors.forename: Fernando
authors.initials: F
authors.lastname: Albericio
authors.affiliation: Institute for Research in Biomedicine, Barcelona Science Park-University of Barcelona, Baldiri i Reixac 10, 08028, Barcelona, Spain. mercedesalvarez@ub.edu.|CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, 08028, Barcelona, Spain. mercedesalvarez@ub.edu.|Laboratory of Organic Chemistry, Faculty of Pharmacy, 08028, Barcelona, Spain. mercedesalvarez@ub.edu.
authors.forename: Mercedes
authors.identifier: 0000-0002-2025-9111
authors.initials: M
authors.lastname: Álvarez
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D001966:Bromine / Q000737:chemistry*; D002074:Butanones / Q000138:chemical synthesis* / Q000737:chemistry; D054879:Halogenation; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D002074:Butanones; D018942:Macrolides; C475799:phormidolide; C057920:3-buten-2-one; D001966:Bromine
keywords: Mukaiyama aldol addition; Wittig olefination; enantioselectivity; natural products; synthesis