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Volumn 3, Issue 6, 2001, Pages 905-908

Synthesis of (±)-epoxysorbicillinol using a novel cyclohexa-2,5-dienone with synthetic applications to other sorbicillin derivatives

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; EPOXIDE; EPOXYSORBICILLINOL;

EID: 0035932578     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0155438     Document Type: Article
Times cited : (50)

References (34)
  • 1
    • 0000745211 scopus 로고
    • For isolation and medicinal value of sorbicillinoids, see: (a) Andrade, R.; Ayer, W. A.; Mebe, P. P. Can. J. Chem. 1992, 70, 2526-2535.
    • (1992) Can. J. Chem. , vol.70 , pp. 2526-2535
    • Andrade, R.1    Ayer, W.A.2    Mebe, P.P.3
  • 17
    • 0042121915 scopus 로고    scopus 로고
    • note
    • A [4 + 2] cycloaddition of 4 produces bisorbicillinol 2, while a net [4 + 4] cycloaddition of 4 results in trichodimerol, see refs 3a,b.
  • 22
    • 0035819289 scopus 로고    scopus 로고
    • There is but one example of an oxidative cyclization occurring with an oxygen nucleophile tethered ortho to the site of cyclization, see: Pelter, A.; Ward, R. S. Tetrahedron 2001, 57, 273-282. For an ipso example, see: Wipf, P.; Kim, Y.; Fritch, P. C. J. Org. Chem. 1993, 58, 7195-7203.
    • (2001) Tetrahedron , vol.57 , pp. 273-282
    • Pelter, A.1    Ward, R.S.2
  • 23
    • 0027772653 scopus 로고
    • There is but one example of an oxidative cyclization occurring with an oxygen nucleophile tethered ortho to the site of cyclization, see: Pelter, A.; Ward, R. S. Tetrahedron 2001, 57, 273-282. For an ipso example, see: Wipf, P.; Kim, Y.; Fritch, P. C. J. Org. Chem. 1993, 58, 7195-7203.
    • (1993) J. Org. Chem. , vol.58 , pp. 7195-7203
    • Wipf, P.1    Kim, Y.2    Fritch, P.C.3
  • 25
    • 0042121916 scopus 로고    scopus 로고
    • note
    • The coefficient of both the C-2 and C-4 sites in the cation are sizable and within striking distance of the tether. However, the coefficient at C-2 is significantly reduced by its proximity to the adjacent carbonyl.
  • 27
    • 0043123852 scopus 로고    scopus 로고
    • note
    • Compound 16 was synthesized in a fashion analogous to that of 13. The X-ray data for 16 has been submitted to the Cambridge Crystallographic database.
  • 31
    • 0043123849 scopus 로고    scopus 로고
    • note
    • We were unable to purify 15; however, replacing the sorbyl side chain with an acetyl residue furnished a mixed ketal presumed to be an analogue of 15.
  • 32
    • 0042623002 scopus 로고    scopus 로고
    • note
    • D of synthetic and natural 2 at similar concentrations.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.