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Volumn 52, Issue 12, 2009, Pages 2176-2179

A facile synthesis of goodyeroside A from (S)-malic acid

Author keywords

Esterification; Glycoside; Goodyeroside A; Lactonization; Protecting group

Indexed keywords

FACILE SYNTHESIS; GOODYEROSIDE A; HEPATOPROTECTIVE; LACTONIZATION; MALIC ACIDS; NATURAL PRODUCTS; PROTECTING GROUP; SPECTRAL DATA; TARGET COMPOUND; TOTAL YIELD;

EID: 75749128646     PISSN: 10069291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-009-0150-8     Document Type: Article
Times cited : (4)

References (19)
  • 1
    • 0033066237 scopus 로고    scopus 로고
    • Phenolic glucosides and a γ-lactone glucoside from the sprouts of Crocus sativus
    • DOI 10.1055/s-1999-14020
    • W. Y. Gao Y. M. Li D. Y. Zhu 1999 Phenolic glucosides and a γ-lactone glucoside from the sprouts of Crocus sativus Planta Med 65 425 427 10.1055/s-1999-14020 1:CAS:528:DyaK1MXktlKmsbw%3D (Pubitemid 29299831)
    • (1999) Planta Medica , vol.65 , Issue.5 , pp. 425-427
    • Gao, W.-Y.1    Li, Y.-M.2    Zhu, D.-Y.3
  • 2
    • 0033920780 scopus 로고    scopus 로고
    • Hepatoprotective aliphatic glycosides from three Goodyera species
    • 1:CAS:528:DC%2BD3cXjvFGnu7Y%3D
    • X. M. Du N. Y. Sun Y. Chen N. Irino Y. Shoyama 2000 Hepatoprotective aliphatic glycosides from three Goodyera species Biol Pharm Bull 23 731 734 1:CAS:528:DC%2BD3cXjvFGnu7Y%3D
    • (2000) Biol Pharm Bull , vol.23 , pp. 731-734
    • Du, X.M.1    Sun, N.Y.2    Chen, Y.3    Irino, N.4    Shoyama, Y.5
  • 3
    • 0003707008 scopus 로고
    • Jiangsu New Medical College. Shanghai Scientific Technologic Publishing House Shanghai
    • Jiangsu New Medical College. Dictionary of the Traditional Chinese Medicines. Shanghai: Shanghai Scientific Technologic Publishing House. 1986. 2283-2286
    • (1986) Dictionary of the Traditional Chinese Medicines , pp. 2283-2286
  • 5
    • 27844521932 scopus 로고    scopus 로고
    • Synthesis of 3-O-β-D-glucopyranosyl-(3R)-hydroxybutanolide (Kinsenoside) and 3-O-β-D-glucopyranosyl-(3S)-hydroxybutanolide (Goodyeroside A)
    • DOI 10.1081/CAR-200050541
    • K. Suzuki N. Suzuki M. Yamaura T. Yoshizawa 2005 Synthesis of 3-O-β-D-glucopyranosyl-(3R)-hydroxybutanolide (kinsenoside) and 3-O-β-D-glucopyranosyl-(3S)-hydroxybutanolide (goodyeroside A) J Carbohy Chem 24 73 84 10.1081/CAR-200050541 1:CAS:528:DC%2BD2MXit1Sktbo%3D (Pubitemid 41642748)
    • (2005) Journal of Carbohydrate Chemistry , vol.24 , Issue.1 , pp. 73-84
    • Suzuki, K.1    Suzuki, N.2    Yamaura, M.3    Yoshizawa, T.4
  • 6
    • 26044438842 scopus 로고    scopus 로고
    • A novel total synthesis of kinsenoside and goodyeroside A relying on the efficient reaction of the chiral 2(5H)-furanones
    • DOI 10.1080/1028602042000324916
    • X. Zhang H. H. Huang Q. H. Chen 2005 A novel total synthesis of kinsenoside and goodyeroside A relying on the efficient reaction of the chiral 2(5H)-furanones J Asian Nat Prod Res 7 5 711 721 10.1080/1028602042000324916 1:CAS:528:DC%2BD2MXhtV2hurbO (Pubitemid 41406416)
    • (2005) Journal of Asian Natural Products Research , vol.7 , Issue.5 , pp. 711-721
    • Zhang, X.1    Huang, H.-H.2    Chen, Q.-H.3
  • 7
    • 73549090605 scopus 로고    scopus 로고
    • Total synthesis of goodyeroside A
    • 1:CAS:528:DC%2BD2cXltVKqtbY%3D
    • X. Zhang Z. Y. Lin Q. H. Chen H. H. Huang 2004 Total synthesis of goodyeroside A Chemistry 67 5 377 379 1:CAS:528:DC%2BD2cXltVKqtbY%3D
    • (2004) Chemistry , vol.67 , Issue.5 , pp. 377-379
    • Zhang, X.1    Lin, Z.Y.2    Chen, Q.H.3    Huang, H.H.4
  • 8
    • 0026559843 scopus 로고
    • A revised mechanism for chemoselective reduction of esters with boranedimethyl sulfide complex and catalytic sodium tetrahydroborate directed by adjacent hydroxyl group
    • 10.1016/S0040-4020(01)92187-8 1:CAS:528:DyaK38XkvV2rs7Y%3D
    • S. Saito T. Ishikawa A. Kuroda K. Koga T. Moriwake 1992 A revised mechanism for chemoselective reduction of esters with boranedimethyl sulfide complex and catalytic sodium tetrahydroborate directed by adjacent hydroxyl group Tetrahedron 48 20 4067 4086 10.1016/S0040-4020(01)92187-8 1:CAS:528:DyaK38XkvV2rs7Y%3D
    • (1992) Tetrahedron , vol.48 , Issue.20 , pp. 4067-4086
    • Saito, S.1    Ishikawa, T.2    Kuroda, A.3    Koga, K.4    Moriwake, T.5
  • 9
    • 0033615630 scopus 로고    scopus 로고
    • Synthesis of the C1-C28 portion of spongistatin 1 (altohyrtin A)
    • DOI 10.1021/jo9910987
    • M. M. Claffey C. J. Hayes C. H. Heathcock 1999 Synthesis of the C1-C28 portion of spongistation 1 (altohyrtin A) J Org Chem 64 8267 8274 10.1021/jo9910987 1:CAS:528:DyaK1MXmsFejtrw%3D (Pubitemid 29529238)
    • (1999) Journal of Organic Chemistry , vol.64 , Issue.22 , pp. 8267-8274
    • Claffey, M.M.1    Hayes, C.J.2    Heathcock, C.H.3
  • 10
    • 0000749329 scopus 로고
    • Combination of borane-dimethyl sulfide complex with catalytic sodium tetrahydroborate as a selective reducing agent for α-hydroxy esters Versatile chiral building block from (s)-(-)-malic acid
    • S. Saito T. Hasegawa M. Inaba R. Nishida T. Fujii S. Nomizu T. Moriwake 1984 Combination of borane-dimethyl sulfide complex with catalytic sodium tetrahydroborate as a selective reducing agent for α-hydroxy esters Versatile chiral building block from (s)-(-)-malic acid. Chem Lett 13 8 1389 1392
    • (1984) Chem Lett , vol.13 , Issue.8 , pp. 1389-1392
    • Saito, S.1    Hasegawa, T.2    Inaba, M.3    Nishida, R.4    Fujii, T.5    Nomizu, S.6    Moriwake, T.7
  • 11
    • 0031041864 scopus 로고    scopus 로고
    • Synthesis of (+)-2,8-dihydroxyethyl-1,4,7,10-tetraoxaspiro[5.5]undecane from (R)-4-hydroxymethyl-2,2-dimethyl-1,3-dioxane
    • DOI 10.1016/S0957-4166(96)00517-4, PII S0957416696005174
    • S. Sauret-Cladiere G. Jeminet 1997 Synthesis of (+)-2,8-dihydroxyethyl-1,4,7,10-tetraoxaspiro[5,5]undecane from (R)-4-hydroxymethyl-2,2-dimethyl-1,3-dioxane Tetrahedron Asymmetry 8 3 417 423 10.1016/S0957-4166(96)00517-4 1:CAS:528:DyaK2sXhsVaqs7w%3D (Pubitemid 27078161)
    • (1997) Tetrahedron Asymmetry , vol.8 , Issue.3 , pp. 417-423
    • Sauret-Cladiere, S.1    Jeminet, G.2
  • 12
    • 0022636075 scopus 로고
    • New methods for the synthesis of glycosides and oligosaccharides- Are there alternatives to the Koenigs-Knorr method?
    • 10.1002/anie.198602121
    • R. R. Schmidt 1986 New methods for the synthesis of glycosides and oligosaccharides- Are there alternatives to the Koenigs-Knorr method? Angew Chem Int Ed Engl 25 212 235 10.1002/anie.198602121
    • (1986) Angew Chem Int Ed Engl , vol.25 , pp. 212-235
    • Schmidt, R.R.1
  • 13
    • 0034644436 scopus 로고    scopus 로고
    • Differential carbohydrate recognition of two GlcNAc-6-sulfotransferases with possible roles in L-selectin ligand biosynthesis
    • DOI 10.1021/ja001224k
    • B. N. Cook S. Bhakta T. Biegel K. G. Bowman J. I. Armstrong S. Hemmerich C. R. Bertozzi 2000 Differential carbohydrate recognition of two GlcNAc-6-sulfotransferases with possible roles in L-selectin ligand biosynthesis J Am Chem Soc 122 36 8612 8622 10.1021/ja001224k 1:CAS:528:DC%2BD3cXlslOksbk%3D (Pubitemid 30703780)
    • (2000) Journal of the American Chemical Society , vol.122 , Issue.36 , pp. 8612-8622
    • Cook, B.N.1    Bhakta, S.2    Biegel, T.3    Bowman, R.G.4    Armstrong, J.I.5    Hemmerich, S.6    Bertozzi, C.R.7
  • 14
    • 0022458594 scopus 로고
    • Sugar stereochemistry and cardiac glycoside activity
    • 10.1021/jm00160a025 1:CAS:528:DyaL28XlsFensb8%3D
    • H. Rathore A. H. L. From K. Ahmed D. S. Fullerton 1986 Sugar stereochemistry and cardiac glycoside activity J Med Chem 29 1945 1952 10.1021/jm00160a025 1:CAS:528:DyaL28XlsFensb8%3D
    • (1986) J Med Chem , vol.29 , pp. 1945-1952
    • Rathore, H.1    From, A.H.L.2    Ahmed, K.3    Fullerton, D.S.4
  • 15
    • 0028186224 scopus 로고
    • Anomeric-oxygen activation for glycoside synthesis: The trichloroacetimidate method
    • 10.1016/S0065-2318(08)60150-X 1:CAS:528:DyaK2MXhslWqtr4%3D
    • R. R. Schmidt W. Kinzy 1994 Anomeric-oxygen activation for glycoside synthesis: the trichloroacetimidate method Adv Carbohydr Chem Biochem 50 21 123 10.1016/S0065-2318(08)60150-X 1:CAS:528:DyaK2MXhslWqtr4%3D
    • (1994) Adv Carbohydr Chem Biochem , vol.50 , pp. 21-123
    • Schmidt, R.R.1    Kinzy, W.2
  • 17
    • 0023222493 scopus 로고
    • A stereoselective approach to the α-lactone fragment of the Lankacidin Antibiotics
    • Thomas E J, Williams A C. A stereoselective approach to the α-lactone fragment of the Lankacidin Antibiotics. J Chem Soc Chem Commun, 1987, 992-994
    • (1987) J Chem Soc Chem Commun , pp. 992-994
    • Thomas, E.J.1    Williams, A.C.2
  • 18
    • 0000253463 scopus 로고    scopus 로고
    • Optically pure dihydroxy γ-alkylated γ-butyrolactones starting from L-tartaric acid: Application to formal and total syntheses of natural products
    • 10.1021/jo970117e 1:CAS:528:DyaK2sXjtlGhsLo%3D
    • A. M. Fernandez J. C. Plaquevent L. Duhamel 1997 Optically pure dihydroxy γ-alkylated γ-butyrolactones starting from L-tartaric acid: Application to formal and total syntheses of natural products J Org Chem 62 4007 4014 10.1021/jo970117e 1:CAS:528:DyaK2sXjtlGhsLo%3D
    • (1997) J Org Chem , vol.62 , pp. 4007-4014
    • Fernandez, A.M.1    Plaquevent, J.C.2    Duhamel, L.3
  • 19
    • 0037155527 scopus 로고    scopus 로고
    • Free-radical-mediated conjugate additions. Enantioselective synthesis of butyrolactone natural products: (-)-Enterolactone, (-)-arctigenin, (-)-isoarctigenin, (-)-nephrosteranic acid, and (-)-roccellaric acid
    • DOI 10.1021/jo015501x
    • M. P. Sibi P. R. Liu J. G. Ji S. Hajra J. X. Chen 2002 Free-Radical-Mediated conjugate additions. Enantioselective synthesis of butyrolactone natural products: (-)-Enterolactone, (-)-arctigenin, (-)-isoarctigenin, (-)-nephrosteranic acid, and (-)-roccellaric acid J Org Chem 67 6 1738 1745 10.1021/jo015501x 1:CAS:528:DC%2BD38XhsVykug%3D%3D (Pubitemid 34246562)
    • (2002) Journal of Organic Chemistry , vol.67 , Issue.6 , pp. 1738-1745
    • Sibi, M.P.1    Liu, P.2    Ji, J.3    Hajra, S.4    Chen, J.-X.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.