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Volumn 45, Issue 41, 2004, Pages 7567-7571

Novel branched ether formation via conjugate reduction of an unsaturated cyanohydrin derivative and its synthetic application to the EF-ring segment of ciguatoxin

Author keywords

Branched ether synthesis; Ciguatoxin; Fused medium ring ether; Hetero Michael addition

Indexed keywords

ALCOHOL; CIGUATOXIN; CYANOHYDRIN; ESTER DERIVATIVE; ETHER; LEWIS ACID; NITRILE;

EID: 4644235621     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.08.117     Document Type: Article
Times cited : (13)

References (59)
  • 1
    • 0035753029 scopus 로고    scopus 로고
    • Reviews for natural cyclic ethers, see: T. Yasumoto Chem. Rec. 3 2001 228
    • (2001) Chem. Rec. , vol.3 , pp. 228
    • Yasumoto, T.1
  • 9
    • 4644270090 scopus 로고
    • Ph.D. Thesis; University of Hawaii
    • (b) Tachibana, K. Ph.D. Thesis; University of Hawaii, 1980
    • (1980)
    • Tachibana, K.1
  • 15
    • 0035239230 scopus 로고    scopus 로고
    • For a review on ciguatera, see: R.L. Lewis Toxicon 39 2001 97
    • (2001) Toxicon , vol.39 , pp. 97
    • Lewis, R.L.1
  • 22
    • 2942557280 scopus 로고    scopus 로고
    • Recent reviews for synthesis of medium cyclic ethers, see: I. Nakamura, and Y. Yamamoto Chem. Rev. 104 2004 2127
    • (2004) Chem. Rev. , vol.104 , pp. 2127
    • Nakamura, I.1    Yamamoto, Y.2
  • 25
  • 46
    • 4644237893 scopus 로고    scopus 로고
    • note
    • Several attempts to reduce selectively the α,β-unsaturated ester part of 15 were unsuccessful
  • 48
    • 4644270256 scopus 로고    scopus 로고
    • note
    • 3P and excess 14 (2.8 equiv) were required to accelerate the reaction rate and to improve the yield
  • 49
    • 4644259213 scopus 로고    scopus 로고
    • note
    • 3Al was ineffective in activating the substrate
  • 52
    • 0000702843 scopus 로고
    • Under the reaction conditions, epoxides 21a and 21b were directly converted to allyl alcohols 22a and 22b, respectively. There were several reports for conversion of 2,3-epoxypropanol derivatives to the corresponding 1-propen-3-ol derivatives under Classon-Samuelsson conditions. For examples: M. Aziz, and F. Rouessac Tetrahedron 44 1988 101
    • (1988) Tetrahedron , vol.44 , pp. 101
    • Aziz, M.1    Rouessac, F.2
  • 56
    • 4644231455 scopus 로고    scopus 로고
    • note
    • In the RCM reaction, 22a was not recovered, and an oligomer that would be resulted from 22a was detected
  • 57
    • 4644363754 scopus 로고    scopus 로고
    • note
    • 2, 58% for three steps; (e) NaH, BnBr, TBAI; (f) TBAF, ̃100% for two steps
  • 58
    • 4644236125 scopus 로고    scopus 로고
    • note
    • Since the RCM reaction of 31a often stopped without completion, this step was repeated once in order to consume 31a completely. Optimization of the step is currently under way
  • 59
    • 4644273659 scopus 로고    scopus 로고
    • note
    • +: 506.2669, found: 506.2650


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.