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

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Chapter 9 2214) Karabatsos, M.C. J. Am. Chem. Soc. 1967, 89 1367.5) Cherest, M.; Felkin,H.; Prudent, N. Tetrahedron Lett. 1968, 2199.6a) Burgi, H.B.; Dunitz,J.D.; Lebin, J.M.; Wipff, G. Tetrahedron1974, 30,1963.6b) Burgi, H.B.; Dunitz,J.D. Acc. Chem. Res. 1983,16,153.6c) Cherest, M.; Prudent, N. Tetrahedron 1980, 36,1599.7) Cherest, M.; Felkin,H.Tetrahedron Lett. 1968, 2205.8a) Morrison, J.D.; Mosher, H.S. Asymmetric Organic ReactionsPrentice Hall; Englewood Cliff, N.Y. 1971.8b) Valentine, D.Jr.; Scott, J.W. Synthesis 1978, 329.8c) Kagan, H.B. Fiaud, J.C. Top. Stereochem. 1978, 10, 175.9) Brown, H.C.;Park, W.S.; Cho, B.T. Ramachandran, P.V. J. Org.Chem, 1987, 52,5406.10) Midland, M.M. Chem. Rev. 1989, 89, 1553.11a) Jones, D.K.; Liotta, D.C. American Chemical Society NationalMeeting, Washinton D.C. Aug. 1992.11b) Jones, D.K.; Liotta, D.C.; Shinkai, I.; Mathre, D.J. J. Org. Chem.1993,58, 799.12) Mathre, D.J.; Thompson, A.S.; Douglas, A.W.; Hoogsteen, D.K.;Carroll, J.D. Carey, E.G.; Grabowski. E.J.J. J. Org. Chem.1993,58,2880.13) Miyashita, A. J. Am. Chem. Soc. 1980, 102,7932.14a) Toriumi, K.; Ito, T.; Takaya, H.; Souchi, T.; Noyori, R. ActaCryst. 1982, 338, 807.14b) Mashima, K.; Kusano, K.; Ohta, T.; Noyori, R. J. Chem. Soc.Chem. Comm. 1989, 1208.15) Cram. D.J.; Cram, J.M. Acc. Chem. Res. 1978,11,8.16) Noyori, Tamino,I.; Tanimoto,Y. J. Am. Chem. Soc.1979,101,3129.17) Ashly, E.C.; Boone, J.R. J. Org. Chem. 1976, 41, 289.17a) Ashly, E.C.; Boone, J.R. J. Org. Chem. 1976, 41,5524.18a) Yamaguchi, S.;Mosher, H.; Pohland,A. J. Am. Chem. Soc.1972,94,9254.18b) Yamaguchi, S.;Mosher, H. J. Org. Chem. 1973, 38, 1870.18c) Brinkmeyer,R.S.; Kapoor,V.M. J.. Am. Chem. Soc.1977,99,8339.
Chapter 9 22218d) Cohen,N.; Lopresti, R.J.; Neukom,C.; Saucy, G. J. Org. Chem.1980,45, 582.19a) Vigneron, J.P.; Jaquet,I. Tetrahedron 1976,32,939.19b) Vigneron, J.P.; Bloy,V. Tetrahedron Lett .1979, 2683.20) Asami, M.; Mukaiama, T. Heterocycles 1979, 12, 499.21a) Sato, T.; Gotoh, Y.; Fujasawa,T. Tetrahedron Lett .1982,42, 4111.21b) Sato, T.; Gotoh, Y.; Wakabayashi, Y.; Fujasawa,T. TetrahedronLett .1983, 24, 4123.22) Yamamoto,K.; Fukushima,.; Nakasak, M. J. Chem. Soc.Chem.Commun. 1984,1490.23) Terashima, S.; Tanno, N.; Koga, K. J. Chem. Soc. Chem.Communn.1980,1026.24) Kawasaki, M.; Suzuki, Y.; Teroshima, S. Chem Lett. 1984, 239.25) Kato, M.; Susabara, K.; Ochi, K.; Akita, M.; Oishhi,T. Chem.Pharm. Bull. 1991, 39, 2458.26) Hu Seo-Rodriguez, J.A.; Berrocol, J.; Gutierrez, B.; Farre', A. J.;Frigola, J. Bioorganic & Medicinal Chem. Lett. 1993, 2, 269.27) Seebach, D.; Beck, A. K.; Roggo, S.; Wamncott, A. Chem Ber.1985, 118, 3673.28) Brown, E.; Penfornis, A.; Bayama, J.; Touet, J. Tetrahedron:Asymmetry 1991, 2, 339.29) Brown, E.; Leze, A.; Touet, J. Tetrahedron: Asymmetry 1992, 3,841.30) Chen, C.S.; Fujimoto,Y.; Girdaukas, G.; Sih, C.J. J.Am. Chem.Soc.1982, 104, 7294.31) Deusnuelle, P. The lipases in: The Enzymes, Boyer P.O. ed. Vol. 7.575. Academic Press New York 1972.32a) Chapusand, C.; Semariva, M. Biochemistry 1976,15 4987.32b) Sarda, L.; Deusnuelle, P. Biochem. Biophys. Acta 1958, 30, 513.32c) Pieterson, W.A.; Vidol, J.C.; Volwerk, J.J; de Haas, G.H.Biochemistry 1974, 13, 1445.33) Deusnuelle, P.; Sarda, L.; Aihard, G. Biochem. Biophys. Acta1960, 37,570.34a) Brady, L.; Brzozowski, A.M.; Derewenda, Z.S.; Dodson, E.;Dodson, G.; Talley, S.; Turkenburg, J.P. Nature 1990, 343, 767.34b) Brady, L.; Brzozowski, A.M.;Lawson, D.M.;Derewenda, Z.S.Biochemistry 1992, 31, 1532.
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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
Page 22 and 23:
Chapter 1 7-bonds 9 . It is now wid
Page 24 and 25:
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
Page 46 and 47:
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
Page 54 and 55:
Chapter 2 39The stereochemistry and
Page 56 and 57:
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
Page 62 and 63:
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
Page 68 and 69:
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
Page 102 and 103:
Chapter 3 87Raney NickelOH Br MeOH;
Page 104 and 105:
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
Page 174 and 175:
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
Page 186 and 187: Chapter 8 171in CH 2 Cl 2 and washe
Page 188 and 189: 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 238 and 239: Chapter 9 22334c) Blow D. Nature 19
Page 240 and 241: Chapter 9 22567a) Kundu, N.G.; Pal,
Page 242: Chapter 9 22712) Thompson,A.S.; Hum
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