title: Synthesis and characterization of all four diastereomers of 3,4-dichloro-2-pentanol, motifs relevant to the chlorosulfolipids.
abstract: All four diastereomers of 3,4-dichloro-2-pentanol were synthesized by anti-dichlorination of the precursor allylic alcohols; their stereochemistry was elucidated by X-ray crystallographic analysis of tosylate derivatives. Complete NMR data is provided in the hope that this information will facilitate structural elucidation and synthesis studies on the chlorosulfolipid family of natural products, such as malhamensilipin A.
authors.affiliation: Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
authors.forename: Jacob S
authors.initials: JS
authors.lastname: Kanady
authors.forename: John D
authors.initials: JD
authors.lastname: Nguyen
authors.forename: Joseph W
authors.initials: JW
authors.lastname: Ziller
authors.forename: Christopher D
authors.initials: CD
authors.lastname: Vanderwal
mesh_terms: D018360:Crystallography, X-Ray; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D008055:Lipids / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D000439:Pentanols / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006843:Hydrocarbons, Chlorinated; D008055:Lipids; D000439:Pentanols; C015518:sulfolipids