title: Stereocontrolled regeneration of olefins from epoxides.
abstract: Through treatment with NaI and trifluoroacetic anhydride, which presumably forms trifluoroacetyl iodidein situ, epoxides can be converted to olefins. This reaction now has been shown to tolerate remote olefins without loss of their individual stereochemistry. A reaction sequence involving regiospecific epoxidation of an isoprenoid alcohol, conversion of the alcohol to an azide, and cycloaddition with an acetylene, followed by conversion of the epoxide back to the original olefin, has allowed stereocontrolled preparation of triazole bisphosphonates with a farnesyl or a geranylgeranyl substituent. This strategy may be applicable selective protection of an alkene in other polyolefins, including substrates for metathesis reactions.
authors.affiliation: Department of Chemistry, The University of Iowa 52242-1294.
authors.forename: Veronica S
authors.initials: VS
authors.lastname: Wills
authors.affiliation: Department of Chemistry, The University of Iowa 52242-1294.
authors.forename: Xiang
authors.initials: X
authors.lastname: Zhou
authors.affiliation: Department of Medicine, Roswell Park Cancer Institute, Buffalo, NY, 14263, U.S.A.
authors.forename: Cheryl
authors.initials: C
authors.lastname: Allen
authors.affiliation: Department of Medicine, Roswell Park Cancer Institute, Buffalo, NY, 14263, U.S.A.
authors.forename: Sarah A
authors.initials: SA
authors.lastname: Holstein
authors.affiliation: Department of Chemistry, The University of Iowa 52242-1294.
authors.forename: David F
authors.initials: DF
authors.lastname: Wiemer
keywords: deoxygenation; epoxide; phosphonate; triazole