Synthesis and characterization of all four diastereomers of 3,4-dichloro-2-pentanol, motifs relevant to the chlorosulfolipids.
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.
Kanady
Jacob S
JS
Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
Nguyen
John D
JD
Ziller
Joseph W
JW
Vanderwal
Christopher D
CD
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
D006843:Hydrocarbons, Chlorinated; D008055:Lipids; D000439:Pentanols; C015518:sulfolipids