title: A short and efficient stereoselective synthesis of the polyhydroxylated macrolactone (+)-aspicillin
abstract: [structures: see text] A short and efficient synthesis of the polyhydroxylated macrolactone (+)-aspicilin 1 using a stereoselective lithium perchlorate mediated addition of allyltributyltin to the equatorially disposed carboxaldehyde of 3 (derived from (R',R',R,S) butane diacetal protected butane tetrol 2) as the key step is described. Terminal group manipulation and Masamune-Roush olefination using phosphonate ester 4 followed by macrocyclization via ring closing metathesis afforded the natural product after partial hydrogenation and global deprotection.
authors.affiliation: Department of Chemistry, University of Cambridge, UK.
authors.initials: DJ
authors.lastname: Dixon
authors.initials: AC
authors.lastname: Foster
authors.initials: SV
authors.lastname: Ley