title: Catalytic asymmetric synthesis of phthioceranic acid, a heptamethyl-branched acid from Mycobacterium tuberculosis.
abstract: The first total synthesis of phthioceranic acid (1) has been achieved by an iterative catalytic asymmetric 1,4-addition protocol. This method provides a robust and high-yielding route for the preparation of 1,3-oligomethyl (deoxypropionate) arrays. After the desired number of methyl groups has been introduced, these arrays can be further functionalized at both ends to polymethyl-substituted lipids such as phthioceranic acid, a heptamethyl-branched fatty acid from the virulence factor Sulfolipid-I (2), found in Mycobacterium tuberculosis.
authors.affiliation: Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborg 4, 9747AG, Groningen, The Netherlands.
authors.forename: Bjorn
authors.initials: B
authors.lastname: ter Horst
authors.forename: Ben L
authors.initials: BL
authors.lastname: Feringa
authors.forename: Adriaan J
authors.initials: AJ
authors.lastname: Minnaard
mesh_terms: D002384:Catalysis; D005227:Fatty Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000737:chemistry*
chemical_list: D005227:Fatty Acids; C522296:phthioceranic acid