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Volumn 17, Issue 4, 2005, Pages 218-232

Synthesis of enantiopure phthalides including 3-butylphthalide, a fragrance component of celery oil, and determination of their absolute configurations

Author keywords

(1S,2R,4R) ( ) CSDP acid; 2 methoxy 2 (1 naphthyl)propionic acid; Absolute configuration; Camphorsultam dichlorophthalic acid; Chiral 1H NMR anisotropy reagent; Chiral auxiliary; Chiral phthalides; Enantioresolution; M NP acid

Indexed keywords

2 METHOXY 2 (1 NAPHTHYL)PROPIONIC ACID; 3 BUTYLPHTHALIDE; 3 PHENYLPHTHALIDE; ALCOHOL DERIVATIVE; CAMPHOR DERIVATIVE; CAMPHORSULTAM DICHLOROPHTHALIC ACID; FRAGRANCE; GLYCOL; IRIDIUM COMPLEX; NAPHTHYL GROUP; PHTHALIDE DERIVATIVE; POTASSIUM HYDROXIDE; PROPIONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; VEGETABLE OIL;

EID: 17844409050     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.20156     Document Type: Article
Times cited : (52)

References (38)
  • 1
    • 17844366909 scopus 로고
    • and references cited therein
    • Ciamician G, Silber. Ber 1897;30:1427 and references cited therein.
    • (1897) Ber , vol.30 , pp. 1427
    • Ciamician, G.1    Silber2
  • 2
    • 0027535709 scopus 로고
    • Chemoprevention of benzo[a]pyrene-induced forestomach cancer in mice by natural phthalides from celery seed oil
    • (a) Zheng G-Q, Kenny PM, Zhang J, Lam LKT. Chemoprevention of benzo[a]pyrene-induced forestomach cancer in mice by natural phthalides from celery seed oil. Nutr Cancer 1993;19:77-86.
    • (1993) Nutr Cancer , vol.19 , pp. 77-86
    • Zheng, G.-Q.1    Kenny, P.M.2    Zhang, J.3    Lkt, L.4
  • 3
    • 0035139052 scopus 로고    scopus 로고
    • Mosquitocidal, nematicidal, and antifungal compounds from Apium graveolens L. seeds
    • (b) Momin RA, Nair MG. Mosquitocidal, nematicidal, and antifungal compounds from Apium graveolens L. seeds. J Agric Food Chem 2001;49:142-145.
    • (2001) J Agric Food Chem , vol.49 , pp. 142-145
    • Momin, R.A.1    Nair, M.G.2
  • 4
    • 55549127608 scopus 로고
    • The constitution of sedanolide
    • and references cited therein
    • Barton DHR, de Vries JX. The constitution of sedanolide. J Chem Soc 1963;1916-1919 and references cited therein.
    • (1963) J Chem Soc , pp. 1916-1919
    • Barton, D.H.R.1    De Vries, J.X.2
  • 5
    • 50549196906 scopus 로고
    • Studies on the constituents of Umbelliferae plants XI, stereochemistry of 3-butylhydrophthalides
    • and references cited therein
    • Nagai U, Shishido T, Chba R, Mistuhashi H. Studies on the constituents of Umbelliferae plants XI, stereochemistry of 3-butylhydrophthalides. Tetrahedron 1965;21:1701-1709 and references cited therein.
    • (1965) Tetrahedron , vol.21 , pp. 1701-1709
    • Nagai, U.1    Shishido, T.2    Chba, R.3    Mistuhashi, H.4
  • 6
    • 2642662166 scopus 로고
    • Enantioface-differentiating addition of a chiral aryllithium reagent to aldehydes
    • Asami M, Mukaiyama T. Enantioface-differentiating addition of a chiral aryllithium reagent to aldehydes. Chem Lett 1980;17-20.
    • (1980) Chem Lett , pp. 17-20
    • Asami, M.1    Mukaiyama, T.2
  • 7
    • 0025143597 scopus 로고
    • Enantioselective synthesis of 4-substituted λ-lactones
    • (a) Ohkuma T, Kitamura M, Noyori R. Enantioselective synthesis of 4-substituted λ-lactones. Tetrahedron Lett 1990;31:5509-5512.
    • (1990) Tetrahedron Lett , vol.31 , pp. 5509-5512
    • Ohkuma, T.1    Kitamura, M.2    Noyori, R.3
  • 8
    • 0026633501 scopus 로고
    • A new asymmetric synthesis of (R)- and (S)-3-arylphthalides: Extremely high diastereoselective reaction of arylcarbaldehydes with chiral [2-(1,3-oxazolidin-2-yl)phenyl]titanium ate complexes
    • (b) Takahashi H, Tsubuki T, Higashiyama K. A new asymmetric synthesis of (R)- and (S)-3-arylphthalides: extremely high diastereoselective reaction of arylcarbaldehydes with chiral [2-(1,3-oxazolidin-2-yl)phenyl]titanium ate complexes. Synthesis 1992;681-684.
    • (1992) Synthesis , pp. 681-684
    • Takahashi, H.1    Tsubuki, T.2    Higashiyama, K.3
  • 9
    • 0029876779 scopus 로고    scopus 로고
    • Efficient general asymmetric syntheses of 3-substituted 1(3H)-isobenzofuranones in very high enantiomeric excess
    • (c) Ramachandran PV, Chen G-M, Brown HC. Efficient general asymmetric syntheses of 3-substituted 1(3H)-isobenzofuranones in very high enantiomeric excess. Tetrahedron Lett 1996;37:2205-2208.
    • (1996) Tetrahedron Lett , vol.37 , pp. 2205-2208
    • Ramachandran, P.V.1    Chen, G.-M.2    Brown, H.C.3
  • 10
    • 0030862303 scopus 로고    scopus 로고
    • Microbial asymmetric syntheses of 3-alkylphthalide derivatives
    • (d) Kitayama T. Microbial asymmetric syntheses of 3-alkylphthalide derivatives. Tetrahedron: Asymmetry 1997;8:3765-3774.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 3765-3774
    • Kitayama, T.1
  • 11
    • 0036422193 scopus 로고    scopus 로고
    • Synthesis of chiral 3-substituted phthalides via rhodium(I)-catalyzed crossed alkyne cyclotrimerisation
    • and references cited therein
    • Witulski B, Zimmermann A. Synthesis of chiral 3-substituted phthalides via rhodium(I)-catalyzed crossed alkyne cyclotrimerisation. Synlett 2002;11:1855-1859 and references cited therein.
    • (2002) Synlett , vol.11 , pp. 1855-1859
    • Witulski, B.1    Zimmermann, A.2
  • 12
    • 33847087351 scopus 로고
    • Reduction of α,β-acetylenic ketones with B-3-pinanyl-9- borabicyclo[3.3.1]nonane. High asymmetric induction in aliphatic systems
    • (a) Midland MM, McDowell DC, Hatch RL, Tramontano A. Reduction of α,β-acetylenic ketones with B-3-pinanyl-9-borabicyclo[3.3.1]nonane. High asymmetric induction in aliphatic systems. J Am Chem Soc 1980;102:867-869.
    • (1980) J Am Chem Soc , vol.102 , pp. 867-869
    • Midland, M.M.1    McDowell, D.C.2    Hatch, R.L.3    Tramontano, A.4
  • 13
    • 0021172960 scopus 로고
    • Enantioselective total synthesis of pumiliotoxin B and pumiliotoxin 251D. A general entry to the pumiliotoxin a alkaloids via stereospecific iminium ion-vinylsilane cyclizations
    • (b) Overman LE, Bell KL, Ito F. Enantioselective total synthesis of pumiliotoxin B and pumiliotoxin 251D. A general entry to the pumiliotoxin A alkaloids via stereospecific iminium ion-vinylsilane cyclizations. J Am Chem Soc 1984;106:4192-4201.
    • (1984) J Am Chem Soc , vol.106 , pp. 4192-4201
    • Overman, L.E.1    Bell, K.L.2    Ito, F.3
  • 14
    • 0005239672 scopus 로고
    • Synthesis and separation of diastereomeric imino alcohol derivatives of chiral phthalides: A method for assignment of phthalide absolute configurations
    • Pirkle WH, Sowin TJ. Synthesis and separation of diastereomeric imino alcohol derivatives of chiral phthalides: a method for assignment of phthalide absolute configurations. J Org Chem 1987;52:3011-3017.
    • (1987) J Org Chem , vol.52 , pp. 3011-3017
    • Pirkle, W.H.1    Sowin, T.J.2
  • 15
    • 0000308203 scopus 로고
    • Revision of the absolute configurations of [8]paracyclophane-10- carboxylic and 15-methyl[10]paracyclophane-12-carboxylic acids
    • (a) Harada N, Soutome T, Nehira T, Uda H, Oi S, Okamura A, Miyano S. Revision of the absolute configurations of [8]paracyclophane-10-carboxylic and 15-methyl[10]paracyclophane-12-carboxylic acids. J Am Chem Soc 1993;115:7547-7548.
    • (1993) J Am Chem Soc , vol.115 , pp. 7547-7548
    • Harada, N.1    Soutome, T.2    Nehira, T.3    Uda, H.4    Oi, S.5    Okamura, A.6    Miyano, S.7
  • 16
    • 0002536852 scopus 로고    scopus 로고
    • Chiral phthalic acid amide, a chiral auxiliary useful for enantiomer resolution and X-ray crystallographic determination of the absolute stereochemistry of alcohols
    • (b) Harada N, Nehira T, Soutome T, Hiyoshi N, Kido F. Chiral phthalic acid amide, a chiral auxiliary useful for enantiomer resolution and X-ray crystallographic determination of the absolute stereochemistry of alcohols. Enantiomer 1996;1:35-39.
    • (1996) Enantiomer , vol.1 , pp. 35-39
    • Harada, N.1    Nehira, T.2    Soutome, T.3    Hiyoshi, N.4    Kido, F.5
  • 17
    • 0030878397 scopus 로고    scopus 로고
    • Chiral dichlorophthalic acid amide, an improved chiral auxiliary useful for enantioresolution and X-ray crystallographic determination of absolute stereochemistry
    • (a) Harada N, Koumura N, Robillard M. Chiral dichlorophthalic acid amide, an improved chiral auxiliary useful for enantioresolution and X-ray crystallographic determination of absolute stereochemistry. Enantiomer 1997;2:303-309.
    • (1997) Enantiomer , vol.2 , pp. 303-309
    • Harada, N.1    Koumura, N.2    Robillard, M.3
  • 18
    • 0032857803 scopus 로고    scopus 로고
    • Enantioresolution and absolute stereochemistry of 2-(1-naphthyl)propane- 1,2-diol and related compounds
    • (b) Kuwahara S, Fujita K, Watanabe M, Harada N, Ishida T. Enantioresolution and absolute stereochemistry of 2-(1-naphthyl)propane-1,2-diol and related compounds. Enantiomer 1999;4:141-145.
    • (1999) Enantiomer , vol.4 , pp. 141-145
    • Kuwahara, S.1    Fujita, K.2    Watanabe, M.3    Harada, N.4    Ishida, T.5
  • 19
    • 0013070694 scopus 로고    scopus 로고
    • Comparison of CD spectra of (2-methylphenyl)-and (2,6-dimethylphenyl) phenylmethanols leads to erroneous absolute configurations
    • Kosaka M, Kuwahara S, Watanabe M, Harada N, Job GE, Pirkle WH. Comparison of CD spectra of (2-methylphenyl)-and (2,6-dimethylphenyl)phenylmethanols leads to erroneous absolute configurations. Enantiomer 2002;7:213-218.
    • (2002) Enantiomer , vol.7 , pp. 213-218
    • Kosaka, M.1    Kuwahara, S.2    Watanabe, M.3    Harada, N.4    Job, G.E.5    Pirkle, W.H.6
  • 22
    • 17844371508 scopus 로고    scopus 로고
    • See Ref. 11b
    • (a) See Ref. 11b.
  • 25
    • 0001253629 scopus 로고    scopus 로고
    • 1H NMR and/or MS spectrometry with complete removal of the kinetic resolution effect
    • 1H NMR and/or MS spectrometry with complete removal of the kinetic resolution effect. Org Lett 2002;4:2699-2702.
    • (2002) Org Lett , vol.4 , pp. 2699-2702
    • Taji, H.1    Watanabe, M.2    Harada, N.3    Naoki, H.4    Ueda, Y.5
  • 26
    • 0037263598 scopus 로고    scopus 로고
    • 1H NMR shift reagent, MαNP acid. Use of HPLC-CD detector
    • 1H NMR shift reagent, MαNP acid. Use of HPLC-CD detector. Chirality 2003;15:295-299.
    • (2003) Chirality , vol.15 , pp. 295-299
    • Kasai, Y.1    Watanabe, M.2    Harada, N.3
  • 27
    • 0345991243 scopus 로고    scopus 로고
    • 1H NMR anisotropy method with a novel chiral auxiliary, MαNP acid
    • 1H NMR anisotropy method with a novel chiral auxiliary, MαNP acid. Chirality 2004;16:13-21.
    • (2004) Chirality , vol.16 , pp. 13-21
    • Nishimura, T.1    Taji, H.2    Harada, N.3
  • 29
    • 33947085552 scopus 로고
    • Nuclear magnetic resonance enantiomer reagents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α- trifluoromethylphenylacetate (MTPA) esters
    • Dale JA, Mosher HS. Nuclear magnetic resonance enantiomer reagents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α- trifluoromethylphenylacetate (MTPA) esters. J Am Chem Soc 1973;95:512-519.
    • (1973) J Am Chem Soc , vol.95 , pp. 512-519
    • Dale, J.A.1    Mosher, H.S.2
  • 31
    • 2142858450 scopus 로고
    • High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids
    • (a) Ohtani I, Kusumi T, Kashman Y, Kakisawa H. High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids. J Am Chem Soc 1991;113:4092-4096.
    • (1991) J Am Chem Soc , vol.113 , pp. 4092-4096
    • Ohtani, I.1    Kusumi, T.2    Kashman, Y.3    Kakisawa, H.4
  • 32
    • 0042665578 scopus 로고    scopus 로고
    • Resolution of 1- and 2-naphthylmethoxyacetic acids, NMR reagents for absolute configuration determination, by use of L-phenylalaninol
    • and references cited therein
    • (b) Arita S, Yabuuchi T, Kusumi T. Resolution of 1- and 2-naphthylmethoxyacetic acids, NMR reagents for absolute configuration determination, by use of L-phenylalaninol. Chirality 2003;15:609-614 and references cited therein.
    • (2003) Chirality , vol.15 , pp. 609-614
    • Arita, S.1    Yabuuchi, T.2    Kusumi, T.3
  • 33
    • 0028339140 scopus 로고
    • New chirality recognizing reagents for the determination of absolute stereochemistry and enantiomeric purity by NMR
    • (a) Seco JM, Latypov Sh, Quinoa E, Riguera R. New chirality recognizing reagents for the determination of absolute stereochemistry and enantiomeric purity by NMR. Tetrahedron Lett 1994;35: 2921-2924.
    • (1994) Tetrahedron Lett , vol.35 , pp. 2921-2924
    • Seco, J.M.1    Latypov, Sh.2    Quinoa, E.3    Riguera, R.4
  • 34
    • 0942277395 scopus 로고    scopus 로고
    • The assignment of absolute configuration by NMR
    • and references cited therein
    • (b) Seco JM, Quinoa E, Riguera R. The assignment of absolute configuration by NMR. Chem Rev 2004;104:17-117 and references cited therein.
    • (2004) Chem Rev , vol.104 , pp. 17-117
    • Seco, J.M.1    Quinoa, E.2    Riguera, R.3
  • 35
    • 0033522731 scopus 로고    scopus 로고
    • Enantioresolution by the chiral phthalic acid method: Absolute configurations of (2-methylphenyl)phenyl-methanol and related compounds
    • (a) Watanabe M, Kuwahara S, Harada N, Koizumi M, Ohkuma T. Enantioresolution by the chiral phthalic acid method: absolute configurations of (2-methylphenyl)phenyl-methanol and related compounds. Tetrahedron: Asymmetry 1999;10:2075-2078.
    • (1999) Tetrahedron: Asymmetry , vol.10 , pp. 2075-2078
    • Watanabe, M.1    Kuwahara, S.2    Harada, N.3    Koizumi, M.4    Ohkuma, T.5
  • 36
    • 0034025755 scopus 로고    scopus 로고
    • Enantioresolution and absolute stereochemistry of o-substituted diphenylmethanols
    • (b) Kuwahara S, Watanabe M, Harada N, Koizumi M, Ohkuma T. Enantioresolution and absolute stereochemistry of o-substituted diphenylmethanols. Enantiomer 2000;5:109-114.
    • (2000) Enantiomer , vol.5 , pp. 109-114
    • Kuwahara, S.1    Watanabe, M.2    Harada, N.3    Koizumi, M.4    Ohkuma, T.5
  • 38
    • 0037062896 scopus 로고    scopus 로고
    • Mild and chemoselective synthesis of lactones from diols using a novel metal-ligand bifunctional catalysts
    • Suzuki T, Monta K, Tsuchida M, Hiroi K. Mild and chemoselective synthesis of lactones from diols using a novel metal-ligand bifunctional catalysts. Org Lett 2002;4:2361-2363.
    • (2002) Org Lett , vol.4 , pp. 2361-2363
    • Suzuki, T.1    Monta, K.2    Tsuchida, M.3    Hiroi, K.4


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