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Volumn 8, Issue 24, 2006, Pages 5585-5587

Total synthesis of (+)-cyanthiwigin AC

Author keywords

[No Author keywords available]

Indexed keywords

CYANTHIWIGIN AC; DITERPENE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; KETONE; UNCLASSIFIED DRUG;

EID: 33846018551     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062304h     Document Type: Article
Times cited : (35)

References (25)
  • 3
    • 0346150290 scopus 로고    scopus 로고
    • Peng, J.; Avery, M. A.; Hamann, M. T. Org. Lett. 2003, 5, 4575-4578. The optical rotation for 2 was not measured due to minute quantities of the material (confirmed with Professor Mark Hamann).
    • (b) Peng, J.; Avery, M. A.; Hamann, M. T. Org. Lett. 2003, 5, 4575-4578. The optical rotation for 2 was not measured due to minute quantities of the material (confirmed with Professor Mark Hamann).
  • 4
    • 17644420655 scopus 로고    scopus 로고
    • Recent syntheses of cyanthiwigin U and other similar families of natural products: (a) Pfeiffer, M.; Phillips, A. J. J. Am. Chem. Soc. 2005, 127, 5334-5335.
    • Recent syntheses of cyanthiwigin U and other similar families of natural products: (a) Pfeiffer, M.; Phillips, A. J. J. Am. Chem. Soc. 2005, 127, 5334-5335.
  • 5
    • 25844518482 scopus 로고    scopus 로고
    • Waters, S. P.; Tian, Y.; Li, Y.-M.; Danishefsky, S. J. J. Am. Chem. Soc. 2005, 127 (39), 13514-13515 and references cited therein.
    • (b) Waters, S. P.; Tian, Y.; Li, Y.-M.; Danishefsky, S. J. J. Am. Chem. Soc. 2005, 127 (39), 13514-13515 and references cited therein.
  • 6
    • 33845996694 scopus 로고    scopus 로고
    • Hajos, Z. G.; Parrish, D. R. Organic Syntheses; Wiley: New York, 1990; Collect. VII, p 363.
    • Hajos, Z. G.; Parrish, D. R. Organic Syntheses; Wiley: New York, 1990; Collect. Vol. VII, p 363.
  • 10
    • 33845995541 scopus 로고    scopus 로고
    • Dimesylate is unstable at rt but can be stored in the refrigerator for a few days: Wasylishen, R. E.; Rice, K. C.; Weiss, U. Can. J. Chem. 1975, 53, 414-417.
    • (c) Dimesylate is unstable at rt but can be stored in the refrigerator for a few days: Wasylishen, R. E.; Rice, K. C.; Weiss, U. Can. J. Chem. 1975, 53, 414-417.
  • 12
    • 0027234426 scopus 로고    scopus 로고
    • The compound 8b was prepared from the commercially available <+-Hajos-Parrish ketone in two steps (70% yield); see: Isaacs, R.; Di Grandi, M. J.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 3938-3941.
    • The compound 8b was prepared from the commercially available <+)-Hajos-Parrish ketone in two steps (70% yield); see: Isaacs, R.; Di Grandi, M. J.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 3938-3941.
  • 19
    • 33845976794 scopus 로고    scopus 로고
    • Reaction with 10% Pd-C gave an ∼5:1 mixture of 5a/5b in small scale reaction. Large-scale reaction gave partial isomerized products which were difficult to reduce.
    • Reaction with 10% Pd-C gave an ∼5:1 mixture of 5a/5b in small scale reaction. Large-scale reaction gave partial isomerized products which were difficult to reduce.
  • 20
    • 33845992311 scopus 로고    scopus 로고
    • The major isomer 5a had confounding conformers which precluded its full assignment.
    • The major isomer 5a had confounding conformers which precluded its full assignment.
  • 24
    • 33845986835 scopus 로고    scopus 로고
    • 13C NMR spectra indicated the formation of tetracylic compound arising from the Michael addition of cyclohexanone enol onto cyclopentenone.
    • 13C NMR spectra indicated the formation of tetracylic compound arising from the Michael addition of cyclohexanone enol onto cyclopentenone.
  • 25
    • 33846002111 scopus 로고    scopus 로고
    • Spectral data of all compounds are consistent with their structures. Yields refer to isolated yields
    • Spectral data of all compounds are consistent with their structures. Yields refer to isolated yields.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.