Relative stereochemistry determination and synthesis of the major chlorosulfolipid from Ochromonas danica.

The relative stereochemistry of the major chlorosulfolipid of the chrysophyte alga Ochromonas danica, to which we have given the name "danicalipin A", is reported. The first synthesis of this lipid, via several stereospecific electrophilic additions to alkenes, serves to corroborate the stereochemical assignment made by NMR spectroscopy. The synthesis strategy described should be applicable to other chlorosulfolipids and should provide access to sufficient material for studies of the lipid's properties and function in membranes.