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Volumn 10, Issue 9, 2008, Pages 1859-1862

Second-generation total synthesis of haterumalide NA using B-alkyl Suzuki-Miyaura coupling

Author keywords

[No Author keywords available]

Indexed keywords

MACROLIDE; MARINE TOXIN;

EID: 48849096587     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800554f     Document Type: Article
Times cited : (30)

References (28)
  • 7
    • 18744411523 scopus 로고    scopus 로고
    • Hoye and Wang first achieved the total synthesis of haterumalide NA (1) itself. Hoye, T. R.; Wang, J. J. Am. Chem. Soc. 2005, 127, 6950.
    • (b) Hoye and Wang first achieved the total synthesis of haterumalide NA (1) itself. Hoye, T. R.; Wang, J. J. Am. Chem. Soc. 2005, 127, 6950.
  • 13
    • 58149195581 scopus 로고    scopus 로고
    • The stereochemistry was determined by NOESY correlations
    • (b) The stereochemistry was determined by NOESY correlations.
  • 17
    • 58149185885 scopus 로고    scopus 로고
    • 3 had no effect in this case.
    • 3 had no effect in this case.
  • 18
    • 58149185887 scopus 로고    scopus 로고
    • We could not recover alkenylsilane 10 under the previous conditions.
    • We could not recover alkenylsilane 10 under the previous conditions.
  • 21
    • 0037078348 scopus 로고    scopus 로고
    • Another macrolactonization, the Shiina conditions, gave only undesired C-3 hydroxy! isomer (12%), see: Shiina, I.; Kubota, M.; Ibuka, R. Tetrahedron Lett. 2002, 43, 7535.
    • Another macrolactonization, the Shiina conditions, gave only undesired C-3 hydroxy! isomer (12%), see: Shiina, I.; Kubota, M.; Ibuka, R. Tetrahedron Lett. 2002, 43, 7535.
  • 23
    • 58149188661 scopus 로고    scopus 로고
    • 5b).
    • 5b).
  • 26
    • 58149192297 scopus 로고    scopus 로고
    • Due to the small reaction scale of Nozaki-Hiyama-Kishi coupling, we could not isolate the minor isomer at C-15.
    • Due to the small reaction scale of Nozaki-Hiyama-Kishi coupling, we could not isolate the minor isomer at C-15.
  • 27
    • 58149184478 scopus 로고    scopus 로고
    • Kobayashi et al. have reported removal of the 2,4-dimethoxybenzyl group in similar esters. Kobayashi, M.; Sato. K.; Yoshimura, S.; Yamaoka, M.; Takase, S.; Ohkubo, M.; Fujii, T.; Nakajima, H. J. Antibiot. 2005, 58, 648.
    • Kobayashi et al. have reported removal of the 2,4-dimethoxybenzyl group in similar esters. Kobayashi, M.; Sato. K.; Yoshimura, S.; Yamaoka, M.; Takase, S.; Ohkubo, M.; Fujii, T.; Nakajima, H. J. Antibiot. 2005, 58, 648.
  • 28
    • 58149177939 scopus 로고    scopus 로고
    • ext 220 nm, Δε +0.10].
    • ext 220 nm, Δε +0.10].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.