OXIDATION CONDITIONS OF CYCLOBUTANOLS
2399
REFERENCES
1
2
. Tojo, G.; Fernandez, M. Oxidation of Alcohols to Aldehydes and Ketones; Springer: Berlin,
006.
2
`
. Aguilera, J.; Guti e´ rrez-Abad, R.; Mor, A.; Moglioni, A. G.; Moltrasio, G. Y.; Ortu n˜ o,
R. M. Stereoselective synthesis of cyclobutyl c-amino acids leading to branched peptides
with a cyclobutane core. Tetrahedron: Asymmetry 2008, 19, 2864–2869.
3
. Matyugina, E. S.; Khandazhinskaya, A. L.; Kochetkov, S. N. Carbocyclic nucleoside
analogues: Classification, target enzymes, mechanisms of action, and synthesis. Russ.
Chem. Rev. 2012, 81, 729–746.
4
. Li, Y.; Mao, S.; Hager, M. W.; Becnel, K. D.; Schinazi, R. F.; Liotta, D. C. Synthesis and
0
evaluation of 2 -substituted cyclobutyl nucleosides and nucleotides as potential anti-HIV
agents. Bioorg. Med. Chem. Lett. 2007, 17, 3398–3401.
5
6
. Bellu ꢀs , D.; Ernst, B. Cyclobutanones and cyclobutenones in nature and in synthesis.
Angew. Chem., Int. Ed. Engl. 1988, 27, 797–827.
. Blanco, J. M.; Caama n˜ o, O.; Fern a´ ndez, F.; Rodriguez-Borges, J. E.; Balzarini, J.;
De Clercq, E. Carbocyclic analogues of nucleosides from bis-(hydroxymethyl)-cyclopentane:
Synthesis, antiviral and cytostatic activities of adenosine, inosine, and uridine analogues.
Chem. Pharm. Bull. 2003, 51, 1060–1063.
7
. Reeder, L. M.; Hegedus, L. S. Effect of b-substituents on the regioselectivity of the
diazomethane ring expansion of a-methyl-a-methoxycyclobutanones to cyclopentanones.
J. Org. Chem. 1999, 64, 3306–3311.
8
9
. Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R.
Synthesis of carbocyclic nucleosides. Tetrahedron 1994, 50, 10611–10670.
. Comin, M. J.; Leitofuter, J.; Rodr ´ı guez, J. B. Enantioselective synthesis of (þ)-neplanocin
F. Tetrahedron 2002, 58, 3129–3136.
1
1
0. Griffith, W. P. Ruthenium oxo complexes as organic oxidants. Chem. Soc. Rev. 1992,
1, 179–185.
1. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. A Greatly improved
procedure for ruthenium tetraoxide–catalyzed oxidations of organic compounds. J. Org.
Chem. 1981, 46, 3936–3938.
2
1
1
1
1
1
1
2. Lee, D. G.; Spitzer, U. A.; Cleland, J.; Olson, M. E. The oxidation of cyclobutanol by
ruthenium tetraoxide and sodium ruthenate. Can. J. Chem. 1976, 54, 2124–2126.
3. Whitney, R. A. A photochemical approach to the synthesis of (ꢃ)-biotin. Can. J. Chem.
1981, 59, 2650–2653.
4. Luzzio, F. A. The oxidation of alcohols by modified oxochromium(VI)-amine reagents.
Org. React. 1998, 53, 1–23.
5. Corey, E. J.; Schmidt, G. Useful procedures for the oxidation of alcohols involving
pyridinium dichromate in aprotic media. Tetrahedron Lett. 1979, 20, 399–402.
6. Xing, X.; Fichera, A.; Kumar, K. A novel synthesis of enantiomerically pure
0 0 0
5
,5,5,5 ,5 ,5 -hexafluoroleucine. Org. Lett. 2001, 3, 1285–1286.
7. Allan, R. D.; Hanrahan, J. R.; Hambley, T. W.; Johnston, G. A. R.; Mewett, K. N.;
Mitrovic, A. D. Synthesis and activity of a potent N-methyl-D-aspartic acid agonist,
trans-l-aminocyclobutane-1,3-dicarboxylic acid, and related phosphonic and carboxylic
acids. J. Med. Chem. 1990, 33, 2905–2915.
1
1
8. Mitra, R. B.; Khanra, A. S. A stereospecific synthesis of methyl (þ)-trans-chrysanthemate
from (þ)-a-pinene. Synth. Commun. 1977, 7, 245–250.
9. Dess, D. B.; Martin, J. C. Readily accessible 12-I-5 oxidant for the conversion of
primary and secondary alcohols to aldehydes and ketones. J. Org. Chem. 1983, 48,
4155–4156.