Stereoselective dichlorination of allylic alcohol derivatives to access key stereochemical arrays of the chlorosulfolipids.
Dichlorination of (Z)-allylic trichloroacetates efficiently and stereoselectively generates the syn,syn hydroxydichloride stereotriad that is prevalent in the understudied polychlorinated sulfolipid class of natural products. Further, the dichlorination of a (Z)-allylic chlorohydrin affords with high selectivity a stereotetrad present in one of the chlorosulfolipids.
Shibuya
Grant M
GM
Department of Chemistry, 1102 Natural Sciences II, The University of California, Irvine, California 92697-2025, USA.
Kanady
Jacob S
JS
Vanderwal
Christopher D
CD
D054879:Halogenation; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis; D008055:Lipids / Q000138:chemical synthesis*; D008968:Molecular Conformation; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
D006843:Hydrocarbons, Chlorinated; D008055:Lipids; D020005:Propanols; C015518:sulfolipids; C006463:allyl alcohol