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.