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Organic Synteses vol 69 - Paquette L.A.

Paquette L.A., Boecman R.K. Organic Synteses vol 69 - John Wiley & Sons, 1990. - 174 p.
ISBN 0-471-54560-0
Download (direct link): organicsynthesesvol691990.pdf
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10. Simon, H.; Bader, J.; G├╝nther, H.; Neumann, S.; Thanos, J. Angew. Chem., Intern. Ed. Engl. 1985, 24, 539.
11. Whitesides, G. M.; Wong, C.-H. Angew. Chem. 1985, 97, 617; Angew. Chem., Intern. Ed. Engl. 1985, 24, 617.
12. Jones, J. B. In "F.E.C.S. Third International Conference on Chemistry and Biotechnology of Biologically Active Natural Products", Sept. 16-21, 1985,
Sofia, Bulgarian Academy of Sciences, Ed.; VCH Publ.: New York, 1987; Vol. 1; pp. 18-39; Breitgoff, D.; Essert, T.; Laumen, K.; Schneider, M. P., Vol. 2, pp. 127-147.
13. See also the three articles on this subject published simultaneously in Chimia: Adachi, K.; Kobayashi, S.; Ohno, M. Chimia 1986, 40, 311; Seebach, D.;
Eberle, M. Chimia 1986, 40, 315; Whitesell, J. K.; Lawrence, R. M. Chimia
1986, 40, 318. For more recent reviews about enzyme catalyzed reactions see: Ohno, M.; Otsuka, M. Org. React. 1989, 37,1; Crout, D. H. G.; Christen, M. in "Modern Synthetic Methods 1989"; Scheffold, R., Ed.; Springer Verlag: Heidelberg, 1989; Chen, C.-S.; Sih, C. J. Angew. Chem. 1989, 101, 711.
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14. Lichtenthaler, F. W.; Nakagawa, T.; El-Scherbiney, A. Chem. Ber. 1968, 101, 1837 (diol); Lichtenthaler, F. W. Chem. Ber. 1963, 96, 845 (diacetate).
15. Baer, H. H.; Shields, D. C.; Dawson, G. G. Can. J. Chem. 1973, 51, 2843.
16. Kn├Âchel, P.; Seebach, D. Nouv. J. Chim. 1981, 5, 75; Kn├Âchel, P.; Seebach, D. Tetrahedron Lett. 1981, 22, 3223; Kn├Âchel, P.; Seebach, D. Tetrahedron Lett. 1982, 23, 3897.
17. Seebach, D.; Kn├Âchel, P. Helv. Chim. Acta 1984, 67, 261.
18. Seebach, D.; Calderari, G.; Kn├Âchel, P. Tetrahedron 1985, 41, 4861.
19. Seebach, D.; Calderari, G.; Meyer, W. L.; Merritt, A.; Odermann, L. Chimia
1985, 39, 183.
20. Blarer, S. J.; Schweizer, W. B.; Seebach, D. Helv. Chim. Acta 1982, 65, 1637; Blarer, S. J.; Seebach, D. Chem. Ber. 1983, 116, 2250 and 3086.
21. Seebach, D.; Imwinkelried, R.; Weber, T. Mod. Synth. Methods 1986, 4, 125-259.
22. Calderari, G.; Seebach, D. Helv. Chim. Acta 1985, 68, 1592, and unpublished results.
23. Seebach, D.; Kalinowski, H. O. Nachr. Chem. Techn. 1976, 24, 415.
24. Seebach, D.; Hungerb├╝hler, E. Mod. Synth. Methods 1980, 91; Conf. Pap. Int. Semin., 2nd 1980, 91-171, Schelfold, R., Ed.; Otto Salle Verlag: Frankfurt/Main, Fed. Rep. Ger.
25. Seebach, D.; Roggo, S.; Zimmermann, J. In "Stereochemistry of Organic and Bioorganic Transformations"; Bartmann, W.; Sharpless, K. B., Eds.; VCH: Weinheim, 1986, New York, 1987; p. 85-126.
26. Ph.D. Thesis of Martin Eberle, ETH Disseration No 8398, Zurich 1987, and part of the projected Dissertation of Martin Missbach.
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Appendix
Chemical Abstracts Nomenclature (Collective Index Number); (Registry Number)
(1S,2S,3R)-3-Hydroxy-2-nitrocyclohexyl acetate: 1,3-Cyclohexanediol, 2-nitro-,
1-acetate, [1S-(1a,2├č,3a)]- (12); (108186-61-4)
(1 R,2r,3S)-2-Nitrocyclohexane-1,3-diol: 1,3-Cyclohexanediol, 2-nitro-, (1a,2├č,3a)- (9); (38150-01-5)
Glutaric dialdehyde: Glutaraldehyde (8); Pentanedial (9); (111-30-8) Nitromethane: Methane, nitro- (8,9); (75-52-5)
Amberlite IR-120(pius) acid form: Amberlite IR 120 Plus (10); (78922-04-0) (1R,2r,3S)-3-Acetoxy-2-nitrocyclohexyl acetate: 1,3-Cyclohexanediol, 2-nitro-, diacetate (ester), (1ot,2├č,3a)- (9); (51269-14-8)
Acetic anhydride (8); Acetic acid anhydride (9); (108-24-7)
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DIASTEREOSELECTIVE FORMATION OF oc-METHOXYCARBONYL LACTONES THROUGH AN INTRAMOLECULAR DIELS-ALDER REACTION: (4RS,4aRS,6RS,8aRS)-, (4S,4aS,6S,8aS)- AND (4R,4aR,6R,8aR)-4-METHOXYCARBONYL-1,1,6-TRIMETHYL-1,4,4a,5,6,7,8,8a-OCTAHYDRO-2.3-BENZOPYRONE [rac-5, (+)-5, and (-)-5]
A.
CHO
O
MeOH, EDDA 15-20┬░C, 45 min
B. 3
H7MeOH 8 hr reflux
CF3COOH, CH2CI2 RT, 48 hr
Submitted by L. F. Tietze, G. v. Kiedrowski, K.-G. Fahlbusch, and E. Voss.1 Checked by Charles F. Marth and Edwin Vedejs.
31
1. Procedure
A. Diels-Alder-adduct rac-3.2 A 250-mL round-bottomed flask equipped with a pressure equalizing addition funnel with a calcium sulfate-filled drying tube, a nitrogen inlet, and a magnetic stirring bar is charged with 2,2-dimethyl-1,3-dioxane-4,6-dione 2 (MeldrumÔÇÖs acid) (Note 1, 10.0 g, 69.4 mmol), a catalytic amount of ethylenediammonium diacetate (EDDA) (Note 2, 500 mg, 2.77 mmol) and dry methanol (150 mL). (R.S)-Citronellal (rac-1, Sigma; dried over MgSO.4 and distilled) (Note 3, 9.74 g = 11.4 mL, 63.1 mmol) is added under nitrogen (Note 4) over 15 min through the dropping funnel to the well-stirred mixture while the temperature is kept at 15-20┬░C by cooling the flask with a water bath. The solution is stirred for an additional 45 min at room temperature, the solvent is removed on a rotary evaporator (25┬░C), and the remaining yellow oil is dissolved in diethyl ether (300 mL). The organic layer is washed with water (50 mL), saturated sodium bicarbonate (2 x 50 mL), and brine (50 mL), and dried over anhydrous sodium sulfate. Filtration and removal of the solvent gives an 8:1-mixture (16.5 g) of the Diels-Alder adduct rac-3 and the ene-product rac-4 as a yellow oil (Note 5).
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