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Volumn 6, Issue 4, 2004, Pages 577-580

Divergent and Stereocontrolled Synthesis of the Enamide Side Chains of Oximidines I/II/III, Salicylihalamides A/B, Lobatamides A/D, and CJ-12,950

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ANTINEOPLASTIC AGENT; BENZOLACTONE ENAMIDE; CJ 12950; COPPER DERIVATIVE; IODINE DERIVATIVE; LACTAM DERIVATIVE; LACTONE DERIVATIVE; LOBATAMIDE A; LOBATAMIDE D; MALEIMIDE; METHOXYAMINE; OXIMIDINE DERIVATIVE; PHOSPHORANE DERIVATIVE; PROPYLIDENETRIPHENYLPHOSPHORANE; SALICYLIHALAMIDE A; SALICYLIHALAMIDE B; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

EID: 1342290256     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036381d     Document Type: Article
Times cited : (82)

References (46)
  • 1
    • 0345134728 scopus 로고    scopus 로고
    • For a review, see: Yet, L. Chem. Rev. 2003, 103, 4283.
    • (2003) Chem. Rev. , vol.103 , pp. 4283
    • Yet, L.1
  • 2
    • 0001087954 scopus 로고    scopus 로고
    • Oximidines I and II: Kim, J. W.; Shin-ya, K.; Furihata, K.; Hayakawa, Y. ; Seto, H. J. Org. Chem. 1999, 64, 153. Oximidine III: Hayakawa, Y.; Tomikawa, T.; Shin-ya, K.; Arao, N.; Nagai, K.; Suzuki, K.-i.; Furihata, K. J. Antibiot. 2003, 56, 905. For an approach to the triene lactone system of oximidine II, see: Coleman, R. S.; Garg, R. Org. Lett. 2001, 3, 3487. For the first total synthesis of oximidine II, see: Wang, X.; Porco, J. A., Jr. J. Am. Chem. Soc. 2003, 725, 6040.
    • (1999) J. Org. Chem. , vol.64 , pp. 153
    • Kim, J.W.1    Shin-ya, K.2    Furihata, K.3    Hayakawa, Y.4    Seto, H.5
  • 3
    • 0344497093 scopus 로고    scopus 로고
    • Oximidines I and II: Kim, J. W.; Shin-ya, K.; Furihata, K.; Hayakawa, Y. ; Seto, H. J. Org. Chem. 1999, 64, 153. Oximidine III: Hayakawa, Y.; Tomikawa, T.; Shin-ya, K.; Arao, N.; Nagai, K.; Suzuki, K.-i.; Furihata, K. J. Antibiot. 2003, 56, 905. For an approach to the triene lactone system of oximidine II, see: Coleman, R. S.; Garg, R. Org. Lett. 2001, 3, 3487. For the first total synthesis of oximidine II, see: Wang, X.; Porco, J. A., Jr. J. Am. Chem. Soc. 2003, 725, 6040.
    • (2003) J. Antibiot. , vol.56 , pp. 905
    • Hayakawa, Y.1    Tomikawa, T.2    Shin-ya, K.3    Arao, N.4    Nagai, K.5    Suzuki, K.-I.6    Furihata, K.7
  • 4
    • 0035515329 scopus 로고    scopus 로고
    • Oximidines I and II: Kim, J. W.; Shin-ya, K.; Furihata, K.; Hayakawa, Y. ; Seto, H. J. Org. Chem. 1999, 64, 153. Oximidine III: Hayakawa, Y.; Tomikawa, T.; Shin-ya, K.; Arao, N.; Nagai, K.; Suzuki, K.-i.; Furihata, K. J. Antibiot. 2003, 56, 905. For an approach to the triene lactone system of oximidine II, see: Coleman, R. S.; Garg, R. Org. Lett. 2001, 3, 3487. For the first total synthesis of oximidine II, see: Wang, X.; Porco, J. A., Jr. J. Am. Chem. Soc. 2003, 725, 6040.
    • (2001) Org. Lett. , vol.3 , pp. 3487
    • Coleman, R.S.1    Garg, R.2
  • 5
    • 0037613530 scopus 로고    scopus 로고
    • Oximidines I and II: Kim, J. W.; Shin-ya, K.; Furihata, K.; Hayakawa, Y. ; Seto, H. J. Org. Chem. 1999, 64, 153. Oximidine III: Hayakawa, Y.; Tomikawa, T.; Shin-ya, K.; Arao, N.; Nagai, K.; Suzuki, K.-i.; Furihata, K. J. Antibiot. 2003, 56, 905. For an approach to the triene lactone system of oximidine II, see: Coleman, R. S.; Garg, R. Org. Lett. 2001, 3, 3487. For the first total synthesis of oximidine II, see: Wang, X.; Porco, J. A., Jr. J. Am. Chem. Soc. 2003, 725, 6040.
    • (2003) J. Am. Chem. Soc. , vol.725 , pp. 6040
    • Wang, X.1    Porco Jr., J.A.2
  • 8
  • 11
    • 0034628240 scopus 로고    scopus 로고
    • (a) Vinyl cuprate addition to an isocyanate: Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407.
    • (2000) Org. Lett. , vol.2 , pp. 407
    • Snider, B.B.1    Song, F.2
  • 15
    • 0034048696 scopus 로고    scopus 로고
    • (e) From an acyl azide via a Curtius rearrangement and subsequent addition of a vinyllithium reagent: Kuramochi, K.; Watanabe, H.; Kitahara, T. Synlett 2000, 397.
    • (2000) Synlett , pp. 397
    • Kuramochi, K.1    Watanabe, H.2    Kitahara, T.3
  • 16
    • 0001572533 scopus 로고    scopus 로고
    • (f) Copper-promoted coupling of a vinyl iodide with a primary amide: Shen, R.; Porco, J. A., Jr. Org. Lett. 2000, 2, 1333.
    • (2000) Org. Lett. , vol.2 , pp. 1333
    • Shen, R.1    Porco Jr., J.A.2
  • 17
    • 0021709385 scopus 로고
    • For the origin of the concept of a divergent synthesis, i.e., the use of a common intermediate to prepare diverse members of a class of synthetic targets or family of natural products, see: Boger, D. L.; Mullican, M. L. J. Org. Chem. 1984, 49, 4045.
    • (1984) J. Org. Chem. , vol.49 , pp. 4045
    • Boger, D.L.1    Mullican, M.L.2
  • 38
    • 1342264232 scopus 로고    scopus 로고
    • note
    • 9d the reaction was performed without ligands and polar aprotic solvents were used, contrasting our reaction conditions.
  • 44
    • 0028324328 scopus 로고
    • For representative examples, see: Busato, S.; Scheffold, R. Helv. Chim. Acta. 1994, 77, 92. Chauhan, K.; Aravind S.; Lee S.-G.; Falck, J. R.; Capdevila, J. H. Tetrahedron Lett. 1994, 35, 6791. Roush, W. R.; Blizzard, T. A. J. Org. Chem. 1983, 48, 758.
    • (1994) Helv. Chim. Acta. , vol.77 , pp. 92
    • Busato, S.1    Scheffold, R.2
  • 46
    • 0009681821 scopus 로고
    • For representative examples, see: Busato, S.; Scheffold, R. Helv. Chim. Acta. 1994, 77, 92. Chauhan, K.; Aravind S.; Lee S.-G.; Falck, J. R.; Capdevila, J. H. Tetrahedron Lett. 1994, 35, 6791. Roush, W. R.; Blizzard, T. A. J. Org. Chem. 1983, 48, 758.
    • (1983) J. Org. Chem. , vol.48 , pp. 758
    • Roush, W.R.1    Blizzard, T.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.