Synthesis and chemistry of 2,3-dioxabicyclo[2.2.2]octane-5,6-diols.

  title={Synthesis and chemistry of 2,3-dioxabicyclo[2.2.2]octane-5,6-diols.},
  author={Peter Valente and Thomas D. Avery and Dennis K. Taylor and Edward R. T. Tiekink},
  journal={The Journal of organic chemistry},
  volume={74 1},
1,4-Disubstituted 2,3-dioxabicyclo[2.2.2]oct-5-enes were dihydroxylated with osmium tetroxide to yield diols anti to the peroxide linkage in a highly selective manner. Reduction of the peroxide bond furnished cyclohexane-1,2,3,4-tetraols with toxocarol relative stereochemistry in excellent yield. This new methodology was employed to synthesize the natural product (1S,2R,3S,4R,5R)-2-methyl-5-(propan-2-yl)cyclohexane-1,2,3,4-tetrol (1) in a short sequence from (R)-alpha-phellandrene. Moreover… Expand
Synthesis of novel tetrols from syn-bisepoxide: Preparation of halogenated bicyclo[4.2.0] inositols
Abstract The synthesis of halogenated bicyclo[4.2.0] inositols (and/or tetrols) are described. The photooxygenation of trans-7,8-dibromobicyclo[4.2.0]octa-2,4-diene obtained using cyclooctatetraeneExpand
Nonbonded Interactions Tune Selectivities in Cycloadditions to 2,3‐Dioxabicyclo[2.2.2]oct‐5‐ene
The facial selectivity of 2,3-dioxabicyclo[2.2.2]oct-5-ene in cycloaddition reactions is distressingly variable and akin to that of 2-oxa-3-azabicyclo[2.2.2]oct-5-ene derivatives. Osmilation takesExpand
Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products
The present review describes the current status of synthetic five and six-membered cyclic peroxides, used in medicine for the design of antimalarial, antihelminthic, and antitumor agents, and the literature from 2000 onwards is surveyed. Expand
Stereospecific synthesis of a dl- gala -aminoquercitol derivative
Abstract A new aminoquercitol derivative was synthesized starting from 1,4-cyclohexadiene. Photooxygenation of cyclohexa-1,4-diene afforded anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-yl hydroperoxide asExpand
Ozonolysis of bicyclic 1,2-dioxines: initial scope and mechanistic insights.
The ozonolysis of bicyclic 1,2-dioxines was investigated using a variety of 1,4-disubstituted 1,3-dialkyl and steroidal example, with yields ranging from moderate to excellent, and initial mechanistic insights into the fragmentation pathways are discussed. Expand
Polyol monoterpenes isolated from Chenopodium ambrosioides
Two new polyol monoterpenes are isolated from stems of Chenopodium ambrosioides on the basis of detailed spectroscopic evidence including extensive 1D and 2D NMR techniques for anti-inflammatory activity and moderate ability to inhibit NO production of LPS-stimulated RAW 264. Expand
The title compound (systematic name: 3,4-dihydroxy-3-phenylfuran-2-one), C10H10O4, features a five-membered γ-lactone ring with an envelope conformation at the C atom carrying the hydroxy groupExpand
In the title compound, C13H22O4, the acetonide ring adopts an envelope conformation with one of the O atoms as the flap atom, whereas a twisted conformation is found for the furanose ring.Expand
Novel sesquiterpenes from Schisandra grandiflora: isolation, cytotoxic activity and synthesis of their triazole derivatives using "click" reaction.
Phytochemical investigation of hexane extract from the fruits of Schisandra grandiflora afforded three novel sesquiterpenes along with the three known compounds, which were studied against Hela, A549, DU-145, MCF-7, and B-16 cancer cell lines. Expand
The title compound, C13H16O, comprises two fused five-membered rings that are linked into a supramolecular chain with a flattened topology via C—H⋯Ohydroxy contacts, and aligned in the a-axis direction. Expand


The Nonclassical Ion Problem
1. That Fascinating Nonclassical Ion Problem.- 1.1. Introduction.- 1.2. Origins.- 1.3. The Nonclassical Ion Era.- 1.4. Steric Assistance.- 1.5. An Alternative Interpretation.- 1.6. The Rococo PeriodExpand
Advanced Organic Chemistry
Organic ChemistryBy Dr. I. L. Finar. Vol. 2: Stereochemistry and the Chemistry of Natural Products. Pp. xi + 733. (London and New York: Longmans, Green and Co., Ltd., 1956.) 40s. net.
however (for it was the literal soul of the life of the Redeemer, John xv. io), is the peculiar token of fellowship with the Redeemer. That love to God (what is meant here is not God’s love to men)Expand
What are “ A ” and “ B ” ?
Direct fabrication of large micropatterned single crystals. p1205 21 Feb 2003. (news): Academy plucks best biophysicists from a sea of mediocrity. p994 14 Feb 2003.
I and i
There is, I think, something ethereal about i —the square root of minus one, which seems an odd beast at that time—an intruder hovering on the edge of reality. Expand
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