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Volumn 1, Issue 7, 2009, Pages 547-551

Total synthesis and study of 6-deoxyerythronolide B by late-stage Cĝ€H oxidation

Author keywords

[No Author keywords available]

Indexed keywords

6 DEOXYERYTHRONOLIDE B; 6-DEOXYERYTHRONOLIDE B; DRUG DERIVATIVE; ERYTHROMYCIN;

EID: 70349556477     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.351     Document Type: Article
Times cited : (172)

References (35)
  • 1
    • 13444287979 scopus 로고    scopus 로고
    • Hydrocarbon oxidation vs. C-C bond-forming approaches for efficient synthesis of oxygenated molecules
    • Fraunhoffer, K. J., Bachovchin, D. A. & White, M. C. Hydrocarbon oxidation vs. C-C bond-forming approaches for efficient synthesis of oxygenated molecules. Org. Lett. 7, 223-226 (2005)
    • (2005) Org. Lett , vol.7 , pp. 223-226
    • Fraunhoffer, K.J.1    Bachovchin, D.A.2    White, M.C.3
  • 2
    • 40949096433 scopus 로고    scopus 로고
    • A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis
    • Chen, M. S. & White, M. C. A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis. Science 318, 783-787 (2007)
    • (2007) Science , vol.318 , pp. 783-787
    • Chen, M.S.1    White, M.C.2
  • 3
    • 33745631495 scopus 로고    scopus 로고
    • Molecular recognition in the selective oxygenation of saturated C-H bonds by a dimanganese catalyst
    • Das, S., Incarvito, C. D., Crabtree, R. H. & Brudvig, G.W. Molecular recognition in the selective oxygenation of saturated C-H bonds by a dimanganese catalyst. Science 312, 1941-1943 (2006)
    • (2006) Science , vol.312 , pp. 1941-1943
    • Das, S.1    Incarvito, C.D.2    Crabtree, R.H.3    Brudvig, G.W.4
  • 4
    • 0037178337 scopus 로고    scopus 로고
    • Catalytic oxidations of steroid substrates by artificial cytochrome P-450 enzymes
    • Yang, J., Gabriele, B., Belvedere, S., Huang, Y. & Breslow, R. Catalytic oxidations of steroid substrates by artificial cytochrome P-450 enzymes. J. Org. Chem. 67, 5057-5067 (2002)
    • (2002) J. Org. Chem. , vol.67 , pp. 5057-5067
    • Yang, J.1    Gabriele, B.2    Belvedere, S.3    Huang, Y.4    Breslow, R.5
  • 5
    • 12344263136 scopus 로고    scopus 로고
    • Late-stage intermolecular C-H activation for lead diversification: A highly chemoselective oxyfunctionalization of the C-9 position of potent bryostatin analogues
    • Wender, P. A., Hilinski, M. K. & Mayweg, A. V. W. Late-stage intermolecular C-H activation for lead diversification: a highly chemoselective oxyfunctionalization of the C-9 position of potent bryostatin analogues. Org. Lett. 7, 79-82 (2005)
    • (2005) Org. Lett. , vol.7 , pp. 79-82
    • Wender, P.A.1    Hilinski, M.K.2    Mayweg, A.V.W.3
  • 6
    • 0028012837 scopus 로고
    • Total synthesis of taxol
    • Nicolaou, K. C. et al. Total synthesis of taxol. Nature 367, 630-634 (1994)
    • (1994) Nature , vol.367 , pp. 630-634
    • Nicolaou, K.C.1
  • 7
    • 0001284819 scopus 로고    scopus 로고
    • The first synthesis of a daphnane diterpene: The enantiocontrolled total synthesis of (+)-resiniferatoxin
    • Wender, P. A. et al. The first synthesis of a daphnane diterpene: the enantiocontrolled total synthesis of (+)-resiniferatoxin. J. Am. Chem. Soc. 119, 12976-12977 (1997)
    • (1997) J. Am. Chem. Soc , vol.119 , pp. 12976-12977
    • Wender, P.A.1
  • 8
    • 0141534438 scopus 로고    scopus 로고
    • A stereoselective synthesis of (-)-tetrodotoxin
    • Hinman, A. & Du Bois, J. A stereoselective synthesis of (-)-tetrodotoxin. J. Am. Chem. Soc. 125, 11510-11511 (2003)
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 11510-11511
    • Hinman, A.1    Du Bois, J.2
  • 9
    • 33644544051 scopus 로고    scopus 로고
    • Combined C-H activation/Cope rearrangement as a strategic reaction in organic synthesis: Total synthesis of (-)-colombiasin A and (-)-elisapterosin B
    • Davies, H. M. L., Dai, X. & Long, M. S. Combined C-H activation/Cope rearrangement as a strategic reaction in organic synthesis: total synthesis of (-)-colombiasin A and (-)-elisapterosin B. J. Am. Chem. Soc. 128, 2485-2490 (2006)
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 2485-2490
    • Davies, H.M.L.1    Dai, X.2    Long, M.S.3
  • 10
    • 0021880919 scopus 로고
    • Recent developments in the total synthesis of macrolide antibiotics
    • Paterson, I. & Mansuri, M. M. Recent developments in the total synthesis of macrolide antibiotics. Tetrahedron 41, 3569-3624 (1985)
    • (1985) Tetrahedron , vol.41 , pp. 3569-3624
    • Paterson, I.1    Mansuri, M.M.2
  • 11
    • 0024801743 scopus 로고
    • Studies in macrolide synthesis: A highly stereoselective synthesis of (+)-(9S)-dihydroerythronolide A using macrocyclic stereocontrol
    • Paterson, I. & Rawson, D. J. Studies in macrolide synthesis: a highly stereoselective synthesis of (+)-(9S)-dihydroerythronolide A using macrocyclic stereocontrol. Tetrahedron Lett. 30, 7463-7466 (1989)
    • (1989) Tetrahedron Lett , vol.30 , pp. 7463-7466
    • Paterson, I.1    Rawson, D.J.2
  • 12
    • 0017850372 scopus 로고
    • Total synthesis of erythromycins. 4. Total synthesis of erythronolide B
    • Corey, E. J. et al. Total synthesis of erythromycins. 4. Total synthesis of erythronolide B. J. Am. Chem. Soc. 100, 4620-4622 (1978)
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 4620-4622
    • Corey, E.J.1
  • 13
    • 0019408557 scopus 로고
    • Asymmetric total synthesis of erythromycin. 1. Synthesis of an erythronolide A seco acid derivative via asymmetric induction
    • Woodward, R. B. et al. Asymmetric total synthesis of erythromycin. 1. Synthesis of an erythronolide A seco acid derivative via asymmetric induction. J. Am. Chem. Soc. 103, 3210-3213 (1981)
    • (1981) J. Am. Chem. Soc. , Issue.103 , pp. 3210-3213
    • Woodward, R.B.1
  • 14
    • 34249058524 scopus 로고    scopus 로고
    • Total synthesis of erythromycin B
    • Breton, P. et al. Total synthesis of erythromycin B. Tetrahedron 63, 5709-5729 (2007)
    • (2007) Tetrahedron , vol.63 , pp. 5709-5729
    • Breton, P.1
  • 16
    • 0025368641 scopus 로고
    • Development of a fully synthetic stereoselective route to 6-deoxyerythronolide B by reiterative applications of the Lewis Acid catalyzed diene aldehyde cyclocondensation reaction: A remarkable instance of diastereofacial selectivity
    • Myles, D. C., Danishefsky, S. J. & Schulte, G. Development of a fully synthetic stereoselective route to 6-deoxyerythronolide B by reiterative applications of the Lewis Acid catalyzed diene aldehyde cyclocondensation reaction: a remarkable instance of diastereofacial selectivity. J. Org. Chem. 55, 1636-1648 (1990)
    • (1990) J. Org. Chem. , vol.55 , pp. 1636-1648
    • Myles, D.C.1    Danishefsky, S.J.2    Schulte, G.3
  • 17
    • 0031747783 scopus 로고    scopus 로고
    • General strategies toward the syntheses of macrolide antibiotics. the total syntheses of 6-deoxyerythronolide B and oleandolide
    • Evans, D. A., Kim, A. S., Metternich, R. & Novack, V. J. General strategies toward the syntheses of macrolide antibiotics. The total syntheses of 6-deoxyerythronolide B and oleandolide. J. Am. Chem. Soc. 120, 5921-5942 (1998)
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 5921-5942
    • Evans, D.A.1    Kim, A.S.2    Metternich, R.3    Novack, V.J.4
  • 18
    • 33744750200 scopus 로고    scopus 로고
    • Formal synthesis of 6-deoxyerythronolide B
    • Crimmons, M. T. & Slade, D. J. Formal synthesis of 6-deoxyerythronolide B. Org. Lett. 8, 2191-2194 (2006)
    • (2006) Org. Lett. , vol.8 , pp. 2191-2194
    • Crimmons, M.T.1    Slade, D.J.2
  • 19
    • 0031271543 scopus 로고    scopus 로고
    • Biosynthesis of erythromycin and rapamycin
    • Staunton, J. & Wilkinson, B. Biosynthesis of erythromycin and rapamycin. Chem. Rev. 97, 2611-2629 (1997)
    • (1997) Chem. Rev. , vol.97 , pp. 2611-2629
    • Staunton, J.1    Wilkinson, B.2
  • 20
    • 0015183169 scopus 로고
    • Stereochemical problems in macrolide antibiotics
    • Celmer, W. D. Stereochemical problems in macrolide antibiotics. Pure Appl. Chem. 28, 413-453 (1971)
    • (1971) Pure Appl. Chem. , vol.28 , pp. 413-453
    • Celmer, W.D.1
  • 23
    • 0030810476 scopus 로고    scopus 로고
    • Pseudoephedrine as a practical chiral auxiliary for the synthesis of highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones
    • Myers, A. G. et al. Pseudoephedrine as a practical chiral auxiliary for the synthesis of highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones. J. Am. Chem. Soc. 119, 6496-6511 (1997)
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 6496-6511
    • Myers, A.G.1
  • 24
    • 0012016624 scopus 로고
    • Enantioselective aldol condensations.Erythro-selective chiral aldol condensations via boron enolates
    • Evans, D. A., Bartroli, J. & Shih, T. L. Enantioselective aldol condensations. Erythro-selective chiral aldol condensations via boron enolates. J. Am. Chem. Soc. 103, 2127-2129 (1981)
    • (1981) J. Am. Chem. Soc , vol.103 , pp. 2127-2129
    • Evans, D.A.1    Bartroli, J.2    Shih, T.L.3
  • 25
    • 0023153093 scopus 로고
    • Concise total synthesis of (+)-(9S)- dihydroerythronolide A
    • Stork, G. & Rychnovsky, S. D. Concise total synthesis of (+)-(9S)- dihydroerythronolide A. J. Am. Chem. Soc. 109, 1565-1567 (1987)
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 1565-1567
    • Stork, G.1    Rychnovsky, S.D.2
  • 26
    • 0000504848 scopus 로고
    • Enantioselective Michael reactions. Diastereoselective reactions of chlorotitanium enolates of chiral N-acyloxazolidinones with representative electrophilic olefins
    • Evans, D. A. et al. Enantioselective Michael reactions. Diastereoselective reactions of chlorotitanium enolates of chiral N-acyloxazolidinones with representative electrophilic olefins. J. Org. Chem. 56, 5750-5752 (1991)
    • (1991) J. Org. Chem. , vol.56 , pp. 5750-5752
    • Evans, D.A.1
  • 27
    • 26944488411 scopus 로고
    • Stereo- and regioselective palladium-catalyzed 1,4-diacetoxylation of 1,3-dienes
    • Bäckvall, J.-E., Byström, S. E. & Nordberg, R. E. Stereo- and regioselective palladium-catalyzed 1,4-diacetoxylation of 1,3-dienes. J. Org. Chem. 49, 4619-4631 (1984)
    • (1984) J. Org. Chem. , vol.49 , pp. 4619-4631
    • Bäckvall, J.-E.1    Byström, S.E.2    Nordberg, R.E.3
  • 28
    • 0031016772 scopus 로고    scopus 로고
    • A remarkable anion effect on the enantioselectivity of the Pd-catalyzed allylic amination using ferrocenyl ligands
    • Burckhardt, U., Baumann, M. & Togni, A. A remarkable anion effect on the enantioselectivity of the Pd-catalyzed allylic amination using ferrocenyl ligands. Tetrahedron Asymmetry 8, 155-159 (1997)
    • (1997) Tetrahedron Asymmetry , vol.8 , pp. 155-159
    • Burckhardt, U.1    Baumann, M.2    Togni, A.3
  • 29
    • 0001616071 scopus 로고
    • A rapid esterification by means of mixed anhydride and its application to large-ring lactonization
    • Inanaga, J., Hirata, K., Saeki, H., Katsuki, T. & Yamaguchi, M. A rapid esterification by means of mixed anhydride and its application to large-ring lactonization. Bull. Chem. Soc. Jpn 52, 1989-1993 (1979)
    • (1979) Bull. Chem. Soc. Jpn , vol.52 , pp. 1989-1993
    • Inanaga, J.1    Hirata, K.2    Saeki, H.3    Katsuki, T.4    Yamaguchi, M.5
  • 30
    • 33748631825 scopus 로고    scopus 로고
    • Assembly-line enzymology for polyketide and nonribosomal peptide antibiotics: Logic, machinery, and mechanisms
    • Fischbach, M. A. & Walsh, C. T. Assembly-line enzymology for polyketide and nonribosomal peptide antibiotics: logic, machinery, and mechanisms. Chem. Rev. 106, 3468-3496 (2006)
    • (2006) Chem. Rev. , vol.106 , pp. 3468-3496
    • Fischbach, M.A.1    Walsh, C.T.2
  • 31
    • 36048958284 scopus 로고    scopus 로고
    • Stereospecificity of ketoreductase domains of the 6-deoxyerythronolide B synthase
    • Castonguay, R., He,W., Chen, A. Y., Khosla, C. & Cane, D. E. Stereospecificity of ketoreductase domains of the 6-deoxyerythronolide B synthase. J. Am. Chem. Soc. 129, 13758-13769 (2007)
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 13758-13769
    • Hew., C.R.1    Chen, A.Y.2    Khosla, C.3    Cane, D.E.4
  • 32
    • 14844357497 scopus 로고    scopus 로고
    • Translation and protein synthesis: Macrolides
    • Katz, L. & Ashley, G. W. Translation and protein synthesis: macrolides. Chem. Rev. 105, 499-527 (2005)
    • (2005) Chem. Rev. , vol.105 , pp. 499-527
    • Katz, L.1    Ashley, G.W.2
  • 33
    • 3042799070 scopus 로고    scopus 로고
    • A planning strategy for diversity-oriented synthesis
    • Burke, M. D. & Schreiber, S. L. A planning strategy for diversity-oriented synthesis. Angew. Chem. Int. Ed. 43, 46-58 (2004)
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 46-58
    • Burke, M.D.1    Schreiber, S.L.2
  • 34
    • 34648829990 scopus 로고    scopus 로고
    • Asymmetric catalysis of the transannular Diels- Alder reaction
    • Balskus, E.P. & Jacobsen, E. N. Asymmetric catalysis of the transannular Diels- Alder reaction. Science 317, 1736-1740 (2007)
    • (2007) Science , vol.317 , pp. 1736-1740
    • Balskus, E.P.1    Jacobsen, E.N.2
  • 35
    • 33748581386 scopus 로고    scopus 로고
    • Site-selective derivatization and remodeling of erythromycin A by using simple peptide-based chiral catalysts
    • Lewis, C. A. & Miller, S. J. Site-selective derivatization and remodeling of erythromycin A by using simple peptide-based chiral catalysts. Angew. Chem. Int. Ed. 45, 5616-5619 (2006)
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 5616-5619
    • Lewis, C.A.1    Miller, S.J.2


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