title: Convergent route to the spirohexenolide macrocycle.
abstract: Using key functional dissections, the synthesis of spirohexenolides is examined through a three-component strategy that features a 1,2-addition to couple tetronate and aldehyde components forming the C2-C3 bond and a Stille coupling to install the third sulfone-containing component. The macrocycle is completed by an intramolecular Julia-Kocienski reaction to form the C10-C11 trans-disubstituted olefin. Application of this strategy is described in progress toward the synthesis of (±)-spirohexenolide B.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, USA.
authors.forename: Brian D
authors.initials: BD
authors.lastname: Jones
authors.forename: James J
authors.initials: JJ
authors.lastname: La Clair
authors.forename: Curtis E
authors.initials: CE
authors.lastname: Moore
authors.forename: Arnold L
authors.initials: AL
authors.lastname: Rheingold
authors.forename: Michael D
authors.initials: MD
authors.lastname: Burkart
mesh_terms: D008958:Models, Molecular; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis*
chemical_list: D013141:Spiro Compounds