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Volumn 38, Issue 29, 1997, Pages 5073-5076

Organozirconocene-mediated polyene synthesis: Preparation of asukamycin and manumycin a side chains

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; ASUKAMYCIN; MANUMYCIN; POLYENE; ZIRCONIUM DERIVATIVE;

EID: 0030745359     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01129-5     Document Type: Article
Times cited : (20)

References (28)
  • 8
    • 0029610989 scopus 로고
    • Lee, M.D.; Fantini, A.A.; Morton, G.O.; James, J.C.; Borders, D.B.; Testa, R.T. J. Antibiot. 1984, 37, 1149. For the total synthesis of (-)-LL-C10037α, see Wipf, P.; Kim, Y.; Jahn, H. Synthesis 1995, 1549.
    • (1995) Synthesis , pp. 1549
    • Wipf, P.1    Kim, Y.2    Jahn, H.3
  • 15
    • 0030607168 scopus 로고    scopus 로고
    • For a review of organozirconocene chemistry, see Wipf, P.; Jahn, H. Tetrahedron 1996, 52, 12853.
    • (1996) Tetrahedron , vol.52 , pp. 12853
    • Wipf, P.1    Jahn, H.2
  • 16
    • 84949159846 scopus 로고
    • Holland, B.C.; Gilman, N.W. Synth. Commun. 1974, 4, 203. A modified workup procedure was employed in which the use of 3N NaOH was omitted.
    • (1974) Synth. Commun. , vol.4 , pp. 203
    • Holland, B.C.1    Gilman, N.W.2
  • 17
    • 0342373031 scopus 로고    scopus 로고
    • 13C NMR, IR and HRMS
    • 13C NMR, IR and HRMS.
  • 19
    • 0342808040 scopus 로고    scopus 로고
    • note
    • 6, 300 MHz) δ 0.75-1.05 (m, 15 H), 1.17 (d, 18 H, J= 7.5 Hz), 1.25-1.75 (m, 15 H), 5.90-6.05 (m, 2 H), 6.25 (dd, 1 H, J = 10, 15 Hz), 6.46 (d, 1 H, J = 18.5 Hz), 6.66 (dd, 1 H, J = 10, 18.5 Hz), 7.51 (dd, 1 H, J = 11.5, 15 Hz).
  • 20
    • 0027441303 scopus 로고
    • Aldehyde 8 was also obtained using zirconocene chemistry via hydrozirconation of ethyl ethynyl ether according to Suzuki's protocol: Maeta, H.; Suzuki, K. Tetrahedron Lett. 1993, 34, 341.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 341
    • Maeta, H.1    Suzuki, K.2
  • 21
    • 0343242597 scopus 로고    scopus 로고
    • Trienyl ester 3 was slightly unstable on silica gel, as were compounds 9, 12, and 4
    • Trienyl ester 3 was slightly unstable on silica gel, as were compounds 9, 12, and 4.
  • 24
    • 0342373029 scopus 로고    scopus 로고
    • Stannane 4 was not obtained analytically pure due to its instability
    • Stannane 4 was not obtained analytically pure due to its instability.
  • 25
    • 0027772653 scopus 로고
    • See, for example: Wipf, P.; Kim, Y.; Fritch, P. C. J. Org. Chem. 1993, 58, 7195. For reviews, see: Bestmann, H. J.; Vostrowski, O. Top. Curr. Chem. 1983, 109, 85. Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
    • (1993) J. Org. Chem. , vol.58 , pp. 7195
    • Wipf, P.1    Kim, Y.2    Fritch, P.C.3
  • 26
    • 0001956611 scopus 로고
    • See, for example: Wipf, P.; Kim, Y.; Fritch, P. C. J. Org. Chem. 1993, 58, 7195. For reviews, see: Bestmann, H. J.; Vostrowski, O. Top. Curr. Chem. 1983, 109, 85. Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
    • (1983) Top. Curr. Chem. , vol.109 , pp. 85
    • Bestmann, H.J.1    Vostrowski, O.2
  • 27
    • 0001848341 scopus 로고
    • See, for example: Wipf, P.; Kim, Y.; Fritch, P. C. J. Org. Chem. 1993, 58, 7195. For reviews, see: Bestmann, H. J.; Vostrowski, O. Top. Curr. Chem. 1983, 109, 85. Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
    • (1989) Chem. Rev. , vol.89 , pp. 863
    • Maryanoff, B.E.1    Reitz, A.B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.