The synthesis of gem-cyclopentyl substituted glutarates via the oxidative ring contraction of 2-acetylcyclohexanones

Synthetic Communications

Volumn 32, Issue 19, 2002, Pages 2911-2918

  Challenger, Stephen ^a   Derrick, Andrew ^a   Silk, Terry V ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

Hydrogen peroxide; Oxidative ring contraction; Preparation of cyclopentyl substituted glutarates

Indexed keywords

1 [2 (BENZYLOXYCARBONYL)ETHYL] 1 CYCLOPENTANECARBOXYLIC ACID; 1 [2 (ETHOXYCARBONYL)ETHYL] 1 CYCLOPENTANECARBOXYLIC ACID; 1 [2 (TERT BUTOXYCARBONYL) 3 (2 METHOXYETHOXY)PROPYL] 1 CYCLOPENTANECARBOXYLIC ACID; 1 [2 (TERT BUTOXYCARBONYL)ETHYL] 1 CYCLOPENTANECARBOXYLIC ACID; 2 ACETYLCYCLOHEXANONE; ACRYLIC ACID DERIVATIVE; CANDOXATRIL; CYCLOHEXANONE DERIVATIVE; CYCLOPENTYLGLUTARATE DERIVATIVE; GLUTARIC ACID DERIVATIVE; HYDROGEN PEROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SYNTHESIS; MELTING POINT; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; THIN LAYER CHROMATOGRAPHY;

EID: 0036383773     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120012979     Document Type: Article

References (12)

1. James, K.; Alabaster, C.T.; Barclay, P.L.; Barnish, I.T.; Blackburn, K.J.; Brown, D.; Campbell, S.F.; Cussans, N.J.; Danilewicz, J.C.; Palmer, M.J.; Terrett, N.K.; Samuels, G.M.R.; Wythes, M.J. Perspectives in Medicinal Chemistry 1993, 45-60.
2. (a) Danilewicz, J.C.; Williams, M.T. European Patent 0342850. Chem. Abs. 1990, 112, 197688;
3. (b) Challenger, S.; Derrick, A.; Mason, C.P.; Silk, T.V. Tetrahedron Lett. 1999, 40, 2187-2190.
4. Mannich, C. Ber. 1941, 74, 1007.
5. Payne, G.B. J. Org. Chem. 1961, 26, 4793-4797.
6. Hawkins, E.G.E.; Large, R. J. Chem. Soc. Perkin I 1973, 19, 2169-2172.
7. Middleton, S.; Stock, L.E. Aust. J. Chem. 1980, 33, 2467-2476.
8. Bruson, H.A.; Rydal, Raterink, H.R. US Patent 2466926. Chem. Abs. 1949, 43, 5417a.
9. Challenger, S. European Patent 391673. Chem. Abs. 1992, 114, 163603; US Patent 5166406. Chem. Abs. 1993, 118, 125106.
10. Challenger, S. European Patent 391673. Chem. Abs. 1992, 114, 163603; US Patent 5166406. Chem. Abs. 1993, 118, 125106.
11. Kryshtal, G.V.; Kulganek, V.V.; Kucherov, V.F.; Yanovskaya, L.A. Synthesis 1979, 2, 107-109.
12. Shanley, E.S. In Organic Peroxides; Swern, D., Ed.; Wiley-Interscience: New York, 1970; Vol. 3, pp. 341-369.