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Volumn 127, Issue 29, 2005, Pages 10396-10399

Stereoselective syntheses of rolliniastatin 1, rollimembrin, and membranacin

Author keywords

[No Author keywords available]

Indexed keywords

OXIDES;

EID: 22944477099     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0526867     Document Type: Article
Times cited : (55)

References (39)
  • 5
    • 0032891112 scopus 로고    scopus 로고
    • For introduction on Annonaceous acetogenins in general, read the following reviews. (e) Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540.
    • (1999) J. Nat. Prod. , vol.62 , pp. 504-540
    • Alali, F.Q.1    Liu, X.-X.2    McLaughlin, J.L.3
  • 21
    • 1542287662 scopus 로고    scopus 로고
    • For selected examples of stereoselective radical cyclization reactions of β-alkoxyacrylates and β-alkoxyvinyl ketones in natural product syntheis, see: (a) Kang, E. J.; Cho, E. J.; Lee, Y. E.; Ji, M. K.; Shin, D. M.; Chung, Y. K.; Lee, E. J. Am. Chem. Soc. 2004, 126, 2680-2681.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 2680-2681
    • Kang, E.J.1    Cho, E.J.2    Lee, Y.E.3    Ji, M.K.4    Shin, D.M.5    Chung, Y.K.6    Lee, E.7
  • 26
    • 0000162105 scopus 로고    scopus 로고
    • Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim
    • For more examples on oxacycle synthesis via radical cyclization, read the following review. (f) Lee E. In Radicals in Organic Synthesis, Vol. 2: Applications; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; pp 303-333.
    • (2001) Radicals in Organic Synthesis, Vol. 2: Applications , vol.2 , pp. 303-333
    • Lee, E.1
  • 32
    • 33444472971 scopus 로고    scopus 로고
    • note
    • Use of ethynyl p-tolyl (R)-sulfoxide (19) in the present synthetic sequence yielded the corresponding oxolanyl product in 98% yield, but the stereoselectivity was lower (mismatched, d.r. = 16:1).
  • 35
    • 33444461139 scopus 로고    scopus 로고
    • note
    • The expected major product was the threo product via chelation model, but the erythro product 11 was the major product in this case.
  • 36
    • 33444470326 scopus 로고    scopus 로고
    • note
    • Synthesis of ent-23 was reported in ref 7.
  • 37
    • 33444469806 scopus 로고    scopus 로고
    • note
    • Use of the intermediates 27 and 28 was reported in ref 4.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.