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Volumn 130, Issue 39, 2008, Pages 13177-13181

Formal synthesis of (-)-kendomycin featuring a prins-cyclization to construct the macrocycle

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN; FORMAL SYNTHESIS; GOOD YIELD; MACROCYCLE; MACROCYCLE FORMATION; MACROCYCLIC RINGS; MODELING STUDIES; PRINS CYCLIZATION; STANDARD METHOD; SUZUKI COUPLINGS; TOTAL SYNTHESIS;

EID: 58149158094     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja805187p     Document Type: Article
Times cited : (105)

References (63)
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    • Funahashi, Y.; Kawamura, N.; Ishimaru, T. Japan Patent 08231551 [A2960910], 1996.
    • (a) Funahashi, Y.; Kawamura, N.; Ishimaru, T. Japan Patent 08231551 [A2960910], 1996.
  • 12
    • 85195236576 scopus 로고    scopus 로고
    • Reviews on the Prins cyclization: (a) Pastor, I. M.; Yus, M. Curr. Org. Chem. 2007, 11, 925-957.
    • Reviews on the Prins cyclization: (a) Pastor, I. M.; Yus, M. Curr. Org. Chem. 2007, 11, 925-957.
  • 14
    • 41049110080 scopus 로고    scopus 로고
    • For leading references on the Prins cyclization, see: a
    • For leading references on the Prins cyclization, see: (a) Elsworth, J. D.; Willis, C. L. Chem. Commun. 2008, 1587-1589.
    • (2008) Chem. Commun , pp. 1587-1589
    • Elsworth, J.D.1    Willis, C.L.2
  • 24
  • 36
    • 0013624593 scopus 로고    scopus 로고
    • The Parikh-Doering conditions gave the best yields after screening a host of standard methods: Parikh, J. R.; Doering, W. v. E. J. Am. Chem. Soc. 1967, 89, 5505-5507.
    • The Parikh-Doering conditions gave the best yields after screening a host of standard methods: Parikh, J. R.; Doering, W. v. E. J. Am. Chem. Soc. 1967, 89, 5505-5507.
  • 38
    • 0041408703 scopus 로고    scopus 로고
    • For recent applications of Hoffmann's powerful boronate 13 in natural product synthesis, see: (b) Rychnovsky, S. D.; Thomas, C. R. Org. Lett. 2000, 2, 1217-1219.
    • For recent applications of Hoffmann's powerful boronate 13 in natural product synthesis, see: (b) Rychnovsky, S. D.; Thomas, C. R. Org. Lett. 2000, 2, 1217-1219.
  • 47
    • 0035980401 scopus 로고    scopus 로고
    • For examples in total synthesis, see: c
    • For examples in total synthesis, see: (c) Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772-10773.
    • (2001) J. Am. Chem. Soc , vol.123 , pp. 10772-10773
    • Liu, P.1    Jacobsen, E.N.2
  • 55
    • 67650568180 scopus 로고    scopus 로고
    • Bahnck, K. B. Ph.D. Dissertation, University of California, Irvine, CA, 2008.
    • Bahnck, K. B. Ph.D. Dissertation, University of California, Irvine, CA, 2008.
  • 58
    • 67650568367 scopus 로고    scopus 로고
    • Two attempts to reproduce Lee's oxidation of diol 2 were unsuccessful in our hands. We are convinced that Lee's oxidation, and the similar oxidation reported by Smith, are valid. However, these transformations proceed through reactive ortho-quinone intermediates and are difficult to conduct.
    • Two attempts to reproduce Lee's oxidation of diol 2 were unsuccessful in our hands. We are convinced that Lee's oxidation, and the similar oxidation reported by Smith, are valid. However, these transformations proceed through reactive ortho-quinone intermediates and are difficult to conduct.
  • 62
    • 67650554662 scopus 로고    scopus 로고
    • See Supporting Information for experimental details
    • See Supporting Information for experimental details.
  • 63
    • 67650568271 scopus 로고    scopus 로고
    • The spectroscopic data for macrocycle 2 matched those reported by Lee and co-workers; the correlation constitutes a formal synthesis of (-)-kendomycin.
    • The spectroscopic data for macrocycle 2 matched those reported by Lee and co-workers; the correlation constitutes a formal synthesis of (-)-kendomycin.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.