Showing papers on "Ferrier rearrangement published in 1999"
TL;DR: The synthesis of (-)-5 was achieved in 15 linear steps (12% overall yield), exploiting a modification of the Petasis-Ferrier rearrangement to construct the C(11-15) cis-tetrahydropyran.
58 citations
TL;DR: This, the second of two Letters, describes the efficient assembly of (+)-4, a C(20-28) subtarget for the total synthesis of phorboxazoles A and B and a new tactic for the synthesis of enol ethers based on the elegant work of Julia is described.
48 citations
TL;DR: In this paper, tri-O acetyl-D-glucal 1 with diverse thiols was treated in the presence of LiBF4 in CH3CN, furnished aryl/alkyl 2,3-unsaturated thioglycopyranosides 8−13 (56-72%).
21 citations
TL;DR: In this paper, the treatment of tri-O acetyl-D-galactal with diverse alcohols in the presence of LiBF4 in CH3CN, furnished alkyl 2,3-unsaturated glycopyranosides 3-18 (50-86%).
18 citations
TL;DR: In this article, asymmetric syntheses of phosphatidylinositol 3-phosphate (PtdIns(3)P) and Ptdins(4)P derivatives are described.
Abstract: New asymmetric syntheses of phosphatidylinositol 3-phosphate (PtdIns(3)P) and phosphatidylinositol 4-phosphate (PtdIns(4)P) derivatives are described. Key intermediates were used to prepare diacylglyceryl moieties with dibutyryl, dioctanoyl, and dihexadecanoyl chains. In addition, a modified route provided PtdIns(3)P and PtdIns(4)P triesters with P-1-linked aminopropyl groups for preparation of affinity probes. The synthesis of the inosityl precursor employed a dibutyltin oxide-mediated p-methoxybenzyl (PMB) etherification to give either the 2-PMB- or the 3-PMB-protected glucopyranosides. The Ferrier rearrangement was used to convert suitably protected glucose derivatives to enantiomerically pure, differentially protected d-myo-inositol key intermediates. A versatile phosphoramidite reagent was employed to allow synthesis of PtdInsPn derivatives with diacylglyceryl moieties of different chain lengths.
7 citations
7 citations
Journal Article•
2 citations
TL;DR: The attempted intermolecular addition of malonyl radicals to 1′,2′-unsaturated nucleosides has led to the unexpected formation of furanones as mentioned in this paper.
Abstract: The attempted intermolecular addition of malonyl radicals to 1′,2′-unsaturated nucleosides has led to the unexpected formation of furanones. Thus, only catalytic amounts of ceric(IV) ammonium nitrate (CAN), induce a Ferrier rearrangement. The unsaturated lactone was isolated in good yield and can serve as a precursor for the synthesis of optically active products.