Stereoselective synthesis of methyl (1R) trans- and (1R) cis-hemicaronaldehydes from natural tartaric acid : application to the synthesis of s-bioallethrin and deltamethrin insecticides
Krief, Alain; University of Namur > Laboratory of Organic Chemistry
Dumont, Willy; University of Namur > Laboratory of Organic Chemistry
Pasau, Patrick; University of Namur > Laboratory of Organic Chemistry
Lecomte, Philippe ; University of Namur > Laboratory of Organic Chemistry
Language :
English
Title :
Stereoselective synthesis of methyl (1R) trans- and (1R) cis-hemicaronaldehydes from natural tartaric acid : application to the synthesis of s-bioallethrin and deltamethrin insecticides
Naumann (1981) Chemie der synthetischen Pyrethroid-Insektizide. Chemie der Pfanzenschutz und Schaldlingsbekampfungsmittel , Springer Verlag, Berlin; 7.
.
Tessier Chem. Ind. (London) 1984, 199.
Ariëns, van Rensen, Welling (1988) Stereoselectivity of Pesticides. Biological and Chemical Problems, Elsevier, Amsterdam; .
Matsui, Yoshioka, Yamada, Sakamoto, Kitahara (1965) Selective Synthesis of Optically Pue (+) and (-)-trans-Chrysanthemic Acids from (+) Δ3-Carene. Agricultural and Biological Chemistry , from Δ3 carene.; 29:784.
Mitra, Khanra (1977) A Stereospecific Synthesis of Methyl (+)-Trans-chrysanthemate from (+)-α-Pinene. Synthetic Communications , from a-pinene.; 7:245.
Fitzsimmons, Fraser-Reid J. Am. Chem. Soc. , from a sugar derivative.; 1979, 101:6123.
Matsuo, Mori, Matsui Tetrahedron Lett. , from Pantolactone.; 1976, 1979.
Ho, Din (1982) Routes totrans-Chrysanthemic Acid. II. Cyclomutative Transformation of (–)–Carvone. Synthetic Communications , from carvone.; 12:257.
Torii, Inokuchi, Oi J. Org. Chem. , from pulegone.; 1983, 48:1944.
Mulzer, Kappert (1983) Diastereo- and Enantioselective Synthesis of (1R,3R)-Caronaldehyde Acid Methyl Ester and (1R,3R)-Chrysanthemic Acid Methyl Ester from (R)-Glycerinaldehyde Acetonide. Angewandte Chemie International Edition in English , from D. Mannitol via D glyceraldehyde.; 22:63.
Krief, Dumont, Pasau Tetrahedron Lett. , from mannitol and L-tartaric acid.; 1988, 29:1079.
Krief, Dumont Tetrahedron Letters , from D-mannitol and L-tartaric acid.; 1988, 29:1083.
Aratani, Yoneyoshi, Nagase Tetrahedron Lett. 1975, 2599.
Aratani, Yoneyoshi, Nagase Tetrahedron Lett. 1975, 1707.
Jakovac, Goodbrand, Lok, Jones (1982) Enzymes in organic synthesis. 24. Preparations of enantiomerically pure chiral lactones via stereospecific horse liver alcohol dehydrogenase catalyzed oxidations of monocyclic meso diols. Journal of the American Chemical Society 104:2244.
Mohr, Waespe-Sarcevic, Tamm, Gawronska, Gawronski (1983) A Study of Stereoselective Hydrolysis of Symmetrical Diesters with Pig Liver Esterase. Helvetica Chimica Acta 66:85.
Schneider, Engel, Hönicke, Heinemann, Görisch (1984) Enzymatic Syntheses of Chiral Building Blocks from Prochiralmeso-Substrates: Preparation of Methyl(hydrogen)-1,2-cycloalkanedicarboxylates. Angewandte Chemie International Edition in English 23:67.
d'Angelo, Revial, Azerad, Buisson J. Org. Chem. 1986, 51:40.
Devos, Hevesi, Bayet, Krief Tetrahedron Lett. 1976, 3911.
Devos, Krief Tetrahedron Lett. 1979, 1511.
Devos, Krief Tetrahedron Lett. 1979, 1515.
Devos, Denis, Krief Tetrahedron Lett. , and ref. cited; 1978, 1847.
Devos, Krief (1982) New synthetic route to (1R)-trans-chrysanthemic ester and to the (1R)-cis-gem-dibromovinyl analog from a common intermediate. Journal of the American Chemical Society 104:4282.
Sevrin, Hevesi, Krief Tetrahedron Lett. 1976, 3915.
Devos, Hevesi, Mathy, Sevrin, Chaboteaux, Krief Organic Synthesis: an Interdisciplinary Challenge , J. Streith, H. Prinzbach, G. Schill, Blackwell Ed., Proceedings of the 5th IUPAC Symposium Freiburg 1984.; 1985, 123.
Babler, Spina Tetrahedron Lett. 1985, 26:1923.
Krief, Hevesi, Chaboteaux, Mathy, Sevrin, Devos (1985) 2-Metallo-2-nitropropanes as isopropylidene transfer reagents for the cyclopropanation of electrophilic alkenes. Application to the synthesis of trans-chrysanthemic acid. Journal of the Chemical Society, Chemical Communications , and references cited; 1693.
Johnson (1966) Ylide Chemistry. Organic Chemistry a series of monographs, Academic Press; .
Grieco, Finkelhor Tetrahedron Lett. 1972, 3781.
Block (1978) Reactions of organosulfur compounds. Organic chemistry a series of monographs, Academic Press; .
Corey, Jautelat J. Am. Chem. Soc. 1967, 89:3912.
Corey, Jautelat, Oppolzer Tetrahedron Lett. 1967, 2325.
Corey, Oppolzer J. Am. Chem. Soc. 1964, 86:1899.
Franzen, Driessen Tetrahedron Lett. 1962, 661.
Franzen, Driessen (1963) Umsetzung von Sulfonium-Yliden mit polaren Doppelbindungen. Chemische Berichte 96:1881.
Trost, Bodganowicz J. Am. Chem. Soc. 1973, 95:5311.
Jurczak, Pikul, Bauer Tetrahedron 1986, 42:447.
Matsunaga, Sakamakjei, Nagoka, Yamada Tetrahedron Lett. 1983, 24:3009.
Trost, Mignani Tetrahedron Lett. 1986, 27:4137.
Mulzer, Kappert Tetrahedron Lett. 1985, 26:1631.
Katsuki, Lee, Ma, Martin, Masamune, Sharpless, Tuddenham, Walker (1982) Synthesis of saccharides and related polyhydroxylated natural products. 1. Simple alditols. The Journal of Organic Chemistry 47:1378.
Stork, Kahn Tetrahedron Lett. 1983, 24:3951.
Yamamoto, Nishii, Ibuka (1987) Diastereoselectivity of conjugate addition to ?-alkoxy-?,?-unsaturated esters via organocopper?Lewis acids and related reagents. Importance of the double bond geometry in controlling the selectivity. Journal of the Chemical Society, Chemical Communications 464.
Roush, Lesur Tetrahedron Lett. 1983, 23:2231.
.
Nadeau, Hanzlik Methods Enzymol. 1969, 15:346.
.
Grawford (1983) Alkylation of enolates from .beta.-dicarbonyl compounds with sulfonium salt electrophiles. The Journal of Organic Chemistry , See for example:; 48:1362.
Minami, Ko, Kishi J. Am. Chem. Soc. 1982, 104:1109.
Rubin, Lardy, Fischer J. Am. Chem. Soc. 1952, 74:425.
Pasau mémoire de licence, Facultés Universitaires N.D. de la Paix; 1986.
.
Hanessian (1983) Total Synthesis of Natural Products: The Chiron Approach. Organic Chemistry Series , J.E. Baldwin, Pergamon Press; 3.
Kagan, Dang J. Am. Soc. 1972, 94:6429.
Katsuki, Sharpless J. Am. Chem. Soc. 1980, 102:5974.
Sharpless, Woodward, Finn Pure and Appl. Chem. 1983, 55:1823.
Lu, Johnson, Finn, Sharpless J. Org. Chem. 1984, 49:728.
Feit J. Med. Chem. 1964, 7:14.
Stork, Nakahara, Greenlee J. Am. Chem. Soc. 1978, 100:7775.
Mori, Takigawa, Matsuo Tetrahedron 1979, 35:933.
Seebach, Hungerbühler Modern Synthetic Methods, E. Scheffold, Otto Salle Verlag, Frankfurt/Main; 1980.
Meyers, Amos J. Am. Chem. Soc. 1980, 102:870.
Hungerbühler, Seebach (1981) Chirale elektrophile Synthesebausteine mit vier verschiedenen funktionellen Gruppen aus Weins�ure, 2, 3- und 3, 4-Epoxy-butandiolderivate in allen vier stereoisomeren Formen. Helvetica Chimica Acta 64:687.
Naef, Seebach (1981) Direct Diastereoselective Alkylation of Tartaric Acid Through an Enolate. Angewandte Chemie International Edition in English 20:1030.
Corey, Marfat, Hoover Tetrahedron Lett. 1981, 22:1587.
Carmack, Kelly J. Org. Chem. 1968, 33:2171.
Wiggins (1946) 4. The acetone derivatives of hexahydric alcohols. Part I. Triacetone mannitol and its conversion into d-arabinose. Journal of the Chemical Society (Resumed) 13.
Fischer (1895) Verbindungen der mehrwerthigen Alkohole mit den Ketonen. Berichte der deutschen chemischen Gesellschaft 28:1167.