Advances in the stereoselective synthesis of antifungal agents and ...

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Chapter 9 22567a) Kundu, N.G.; Pal, M.; Mahanty,J.S.; Dasgupta, S.K. J. Chem.Soc.,Chem. Commun. 1992, 16, 1162.67b) Kundu, N.G.; Mahanty,J.S.; Das, P.; Das, B. Tetrahedron Lett.1993, 34, 10, 1625.68) Larock, R.C.; Yum, E.K.;Doty, M.J.; Sham, K.K.C. J. Org. Chem.1995, 60, 3270.69) Ohemeng, K.A.; Appollina, M.A.; Nguyen, V.N.; Schwender, C.F.;Singer, M.; Steber, M.; Ansell, J.; Argentieri,D,; Hageman, W.J.Med.Chem. 1994, 37, 3663.3.6 References chapter 3:1) Friedel-Crafts and related reactions; Wiley: New York 1963-1964;as Follows Vol. 1, 91-115; Peto, 535-910; Sethna, 911-1002;Goldman, 1003-1032.2) Gore. Chem. Ind. (London). 1974,727-731.3) Larock.Comprehensive organic transformations; VCH: New York,1989,703-704.4) Yamanase,K. Bull. Chem. Soc. Jpn. 1961, 34,480.5) Le Carpentier, J.; Weiss, B. J. Am. Chem. Soc. 1972, 94, 5718.6) review Chevrier; Weiss, B. Angew. Chem. Int. Ed. Engl. 1974,13,1-10.7) Taylor. Electrophilic Aromatic Substitution. New York, 1990, 222-237.8) Oulevelyu; Susz. Helv. Chim. Acta 1964, 47, 1828.9) Ton,E.K.; Brownstein, S. J. Org. Chem. 1983, 43, 302.10) Corriu,E.; Dore,A.; Thomassin,F. Tetrahedron 1971, 27,5601,5819.11) Satchell,M. J. Chem.Soc. 1961, 5404.12) Theophanides, A.; Can. J. Chem. 1970, 48, 3860.14) Wigfield,D.C.V.; Gowland, F.W. J. Org. Chem. 1977, 42, 1108.15) Ashly, E.C.; Boone,C.G.R. J. am. Chem. Soc. 1976, 98, 5524.16) Kayser,M.M.; Elies,S.; Einsten, O. Tetrahedron Lett. 1983, 24,1015.25) Brown, E.; Penfornio, A.; Bayama, J.; Touet, J. Tetrahedron:Asymmetry 1991, 2,339.
Chapter 9 22626) Brown, E.; Lézé, A.; Touet, J.Tetrahedron: Asymmetry 1992,3,841.27) For review, see Hudlicky Reduction in organic Chemistry.28) Jaffard, C.W.; Kirkpatric, D.; Delay, F. J. Am. Chem. Soc. 1977,94,8905.29) Karabatsos,F., Shone,M. J. Org. Chem. 1968, 33, 619.30) Ricci, A.; Danieli, R.; Pivazzini,G. Gazz. Chim. Ital. 1975, 105,37.31) Neumann, P. Synthesis 1987, 47, 665-583.32) Shapiro,P.; Lorenz,D.H.; Stern,A.; Becker,E.I. J. Org. Chem.1963, 28, 2332.33) Colan,P. J. Org. Chem. 1982, 47, 2622.34) Subba Rao; Mukkanti; Choudary. J. Organomet. Chem. 1989,367,C29.35) Narisada;, M. Horibe,I.; Watanabe,F.; Takeba,K. J. Org. Chem.1989, 54,5308.36) Buu-Hoi,Y.; Xuong,J. Bull. Soc. Chim. Fr. 1963, 2442.References Chapter 4.1) Mitsunobu, O. Synthesis 1981,12) Cristalli, P.L. Prog. Nucl. Magn. Reson. Spect.. 1982, 15, 291.3) Wohl, A.; Markwald,W. Ber. 1892,25, 2354.4) Sorrel,T.N.; Allen,W.E. J. Org.Chem. 1994,5 1589 and referencescited therein.5) Cristalli, G.; Eleutieri,A.; Franchetti, P.; Grifantini, M.; Vittori,S.; Lupidi, G. J. Med. Chem. 1991, 34, 1187.6) Mitsunobu, O.; Wada, M.; Sano, T. J.Am. Chem. Soc. 1972, 94679.7) Hughes, D.L. Org. React. 1992, 42, 335.8) Laibner, H.; Zbirol, E. Helv. Chim. Acta 1977, 60, 417.9) Chen,C-P.; Prasad, K.; Repec,O. Tetrahedron Lett. 1991, 32,7175.10) Lal, B.; Pramanik, B.N.; Manhas, M.S.; Bose, A.K. TetrahedronLett. 1977,1977.11) Viaud, M.C.; Rolling, P. Synthesis 1990, 130.
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Advances in the stereoselectivesynt
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ACKNOWLEDGMENT:I would like to than
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Summary:Numerous drugs are chiral,
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IndexII2.2 Synthesis of enantiopure
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IndexIV4.4. Stereochemical Assignme
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IndexVImethyl amine 69 1446.6. Stud
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IndexVIII8.23.3.1 Desilylation usin
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Chapter 1 11.Introduction1.1. Chira
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Chapter 1 3The concept of stereoche
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Chapter 1 5switches is in the area
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Chapter 1 7-bonds 9 . It is now wid
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Chapter 1 914CH 3Cyt P-450 DMOH3O 2
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Chapter 1 11piperazine) is also the
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Chapter 1 13The four stereoisomers
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Chapter 1 15single enantiomers and
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Chapter 1 17was synthesized by the
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Chapter 1 19HOHODesmolaseHOCholeste
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Chapter 1 21formic acid results in
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Chapter 1 23inactivation. 113 . Bec
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Chapter 1 25Two newer compounds whi
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Chapter 1 2715 is an advanced repre
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Chapter 1 29transformation of the a
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Chapter 1 31Enantioselective synthe
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Chapter 1 33+R,S DRUG ANCHOR R MOLE
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Chapter 1 35solubilized in hot etha
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Chapter 2 37RsORmRmRsRLRL RRRLH - A
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Chapter 2 39The stereochemistry and
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Chapter 2 41An asymmetric reducing
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Chapter 2 43This approach clearly e
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Chapter 2 45PhaxeqP 1MP 2axeqPhP 2M
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Chapter 2 47pyrrolidine ] 20 , LAH-
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Chapter 2 49Enzymatic reactions are
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Chapter 2 51As [ES] in equation 4 c
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Chapter 2 53E+AK 1AK -1AEAK 2AE+PE+
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Chapter 2 552.2.4 Lipases.Most lipa
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Chapter 2 57enzyme intermediate can
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Chapter 2 59projecting above the pl
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Chapter 2 612.3.1.1. Step 1: Adduct
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Chapter 2 63A -+ ROHRO - + AH'RO 2
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Chapter 2 65There are various effec
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Chapter 2 67The reactions were foun
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Chapter 2 69Yamanaka and coworkers
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Chapter 2 71sodium or potassium car
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Chapter 3 73The reaction is quite s
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Chapter 3 75literature as the best
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Chapter 3 77dry solvents and, is ch
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Chapter 3 79XXOH+ H 2 NDry K 2 CO 3
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Chapter 3 81substituents are the mo
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Chapter 3 83induces a rotation of t
Page 100 and 101:
Chapter 3 85very sharp and it was p
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Chapter 3 87Raney NickelOH Br MeOH;
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Chapter 4 8933a-m were hydrolysed t
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Chapter 4 91benzo[b]furane (entries
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Chapter 4 93hydroxy or amine groups
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Chapter 4 95the products with ethyl
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Chapter 4 97NCO 2 HNCO 2 H(±)34c(-
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Chapter 4 99NNH37CO2EtOH(±)-27a(+)
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Chapter 4 101As already outlined ab
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Chapter 4 103(+)-(S)-2-octylimidazo
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Chapter 4 105CNNH N2 NCN nC 6 H 13N
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Chapter 4 107key step is the conver
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Chapter 4 109reverse addition in th
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Chapter 4 111which was eliminated e
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Chapter 4 113separate (±)-57a and
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Chapter 5 115to avoid this side rea
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Chapter 5 117Complete degradation o
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Chapter 5 119Entry R T °C Product
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Chapter 5 1212:1:3 in weight. All t
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Chapter 5 123reaction conditions we
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Chapter 5 125Entry Substrate R Time
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Chapter 5 127experiments. But it wa
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Chapter 5 129OClOSAM IIPH=7; R.T.OH
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Chapter 5 131OHOXHOHRHK 2 CO 3 ; Me
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Chapter 6 133HCuSO 4 .5H 2 O,NH 4 O
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Chapter 6 1356.2.1 Heteroannullatio
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Chapter 6 137This discovery allowed
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Chapter 6 139OH(±)-62OHFigure 6.1
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Chapter 6 141Entry Substrate R Time
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Chapter 6 143HOH58-a-c,e,h-lRPdCl 2
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Chapter 6 145afforded the benzo[b]f
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Chapter 6 147RR[P(Ph) 3 ]Pd°OHOPh
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Chapter 6 149H2-IodophenolOHOH(±)-
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Chapter 6 151presence of base as de
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Chapter 7 153A chiral lithium alumi
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Chapter 7 155derivatives were tried
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Chapter 7 157Finally an hypothesis
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Chapter 8 159were washed with a sat
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Chapter 8 16145 min, the mixture wa
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Chapter 8 1638.9 Decarboxylation of
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Chapter 8 165Alcohol 27a (0.2 mmol)
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Chapter 8 167for 48 h. After coolin
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Chapter 8 169room temperature for t
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Chapter 8 171in CH 2 Cl 2 and washe
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Chapter 8 1738.26 Screening of lipa
Page 190 and 191: Chapter 8 175Na 2 SO 4 . After remo
Page 192 and 193: Chapter 8 177NMR and MS analysis we
Page 194 and 195: Chapter 8 179Argon was bubbled thru
Page 196 and 197: Chapter 8 181IR (CHCl 3 ): ν cm-1=
Page 198 and 199: Chapter 8 183GC-MS: 305 M + (68%),
Page 200 and 201: Chapter 8 185[α] 20 D -5.7 (c 1.75
Page 202 and 203: Chapter 8 187Synthetic method 7.7.1
Page 204 and 205: Chapter 8 189(R,S)-(±)-1-(2-Octyl)
Page 206 and 207: Chapter 8 191M.P. = oil.Elementary
Page 208 and 209: Chapter 8 193Synthetic method 7.11.
Page 210 and 211: Chapter 8 195(±)-N-1-(2-Octyl)-2-t
Page 212 and 213: Chapter 8 197IR (CHCl 3 ) ν cm-1 =
Page 214 and 215: Chapter 8 199(±)-1-(4-Fluorophenyl
Page 216 and 217: Chapter 8 201Physical and spectral
Page 218 and 219: Chapter 8 203(±)-1-(Phenyl)-2-prop
Page 220 and 221: Chapter 8 205128.61, 128.87, 130.39
Page 222 and 223: Chapter 8 207min.Physical and spect
Page 224 and 225: Chapter 8 20913C J MOD NMR (CDCl 3
Page 226 and 227: Chapter 8 211(±)-2'-Methylphenyl-2
Page 228 and 229: Chapter 9 213References chapter 1:1
Page 230 and 231: Chapter 9 21531) De Felice, R.; Joh
Page 232 and 233: Chapter 9 21768) Brodie, A.M.H. in
Page 234 and 235: Chapter 9 219112) Brodie, A. M. H.;
Page 236 and 237: Chapter 9 2214) Karabatsos, M.C. J.
Page 238 and 239: Chapter 9 22334c) Blow D. Nature 19
Page 242: Chapter 9 22712) Thompson,A.S.; Hum
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