Synthesis of novel phenoxy-linked diazirine glycero- and sphingolipid probes via trialkylaryltin intermediates

Two photoaffinity lipid probes, phosphatidylcholine analog 1 and ceramide analog 2, were synthesized via trialkylaryltin intermediates 10b,b′ using a Stille coupling strategy. The latter are stable for months at −20°C. Iododestannylation afforded lipid probes 1 and 2.