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Volumn , Issue 3, 2000, Pages 335-338

Biomimetic construction of fused tricyclic ether by cascaded endo- cyclization of the hydroxy triepoxide

Author keywords

Biogenesis; Cascade cyclization; Hydroxy polyepoxides; Lanthanum(III) triflate; Polycyclic ethers

Indexed keywords

EPOXIDE; ETHER DERIVATIVE; LANTHANUM;

EID: 0034052758     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (50)

References (62)
  • 20
    • 0028812058 scopus 로고
    • For a review, see: (a) Koert, U. Synthesis 1995, 115.
    • (1995) Synthesis , pp. 115
    • Koert, U.1
  • 22
    • 0343259397 scopus 로고
    • For formation of tetrahydrofuran systems by cascade reaction of poly epoxides, see: (c) Weitemeyer, C.; de Meijere, A. Angew. Chem. 1976, 88, 721.
    • (1976) Angew. Chem. , vol.88 , pp. 721
    • Weitemeyer, C.1    De Meijere, A.2
  • 49
    • 0033574560 scopus 로고    scopus 로고
    • For the effect of the hydroxy group adjacent to the epoxide in the brevetoxin models, see: (n) Kelly, D. R.; Nally, J. Tetrahedron Lett. 1999, 40, 3251.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 3251
    • Kelly, D.R.1    Nally, J.2
  • 55
    • 0342824579 scopus 로고    scopus 로고
    • note
    • Although the relative configurations of these hydroxy diepoxides 4a, 4b, and triepoxide 5 could not be determined at this stage, they were assigned from those of the resulting cyclic ethers after the cyclization. The absolute configuration of chiral triepoxide 5 is not able to be determined yet.
  • 56
    • 0342824577 scopus 로고    scopus 로고
    • note
    • -1.
  • 57
    • 0342824578 scopus 로고    scopus 로고
    • 1H NMR.
    • 1H NMR.
  • 59
    • 0343259394 scopus 로고    scopus 로고
    • note
    • The corresponding chiral epoxidation of 12 under the similar conditions to the case of 17 led to formation of the chiral antidiepoxide (A) corresponding to 13a in an 83% isolated yield, though the absolute configuration is not able to be determined yet. (Equation presented) Scheme 6
  • 60
    • 0343259393 scopus 로고    scopus 로고
    • note
    • 5 (M), 260.1624, found 260.1621.
  • 62
    • 0342824575 scopus 로고    scopus 로고
    • note
    • 7 (M), 360.2148, found 360.2143.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.