title: Synthesis, structure revision, and absolute configuration of (+)-didemniserinolipid B, a serinol marine natural product from a tunicate Didemnum sp.
abstract: [structure: see text] En route to proving the absolute and relative stereochemistry, through synthesis, of (+)-didemniserinolipid B (1), the first natural serinolipid isolated from a tunicate Didemnum sp., it was discovered that the isolated natural product was in fact the 31-sulfate configured 8R,9R,10R,13S,30S. This structural reassignment was only possible after the development of a microwave-assisted method for the sulfation of unreactive hydroxyl groups.
authors.affiliation: Department of Chemistry, University of Cambridge, UK.
authors.forename: Hiromasa
authors.initials: H
authors.lastname: Kiyota
authors.forename: Darren J
authors.initials: DJ
authors.lastname: Dixon
authors.forename: Christine K
authors.initials: CK
authors.lastname: Luscombe
authors.forename: Stephan
authors.initials: S
authors.lastname: Hettstedt
authors.forename: Steven V
authors.initials: SV
authors.lastname: Ley
mesh_terms: D000818:Animals; D001685:Biological Factors / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D011409:Propylene Glycols / Q000138:chemical synthesis* / Q000737:chemistry*; D014561:Urochordata / Q000737:chemistry*
chemical_list: D001685:Biological Factors; D011409:Propylene Glycols; C467921:didemniserinolipid B