title: Biomimetic synthesis of petuniasterone D via the epoxy ester[bond]ortho ester rearrangement.
abstract: The side chain of the insecticidal steroid petuniasterone D was synthesized by the biomimetic acid-catalyzed epoxy ester[bond]ortho ester rearrangement. In addition to the natural (22R,24R)-configuration of the side chain ortho ester, compounds bearing the epimeric (22R,24S)-, (22S,24R)-, and (22S,24S)- [3.2.1]-bicyclic ortho esters were also produced by stereospecific rearrangement of the corresponding isomeric epoxy esters. Functionalization of the steroid nucleus of the (22R,24R)-ortho ester completed the synthesis of the natural product.
authors.affiliation: Department of Chemistry, SUNY-ESF, Syracuse, New York 13210, USA.
authors.forename: Juan A
authors.initials: JA
authors.lastname: Faraldos
authors.forename: José-Luis
authors.initials: JL
authors.lastname: Giner