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Volumn 47, Issue 14, 2006, Pages 2299-2304

A formal synthesis of aflatoxin B2: A Dötz benzannulation approach

Author keywords

Aflatoxin; Benzannulation; Carbene; Chromium; D tz

Indexed keywords


EID: 33644763028     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.024     Document Type: Article
Times cited : (24)

References (94)
  • 40
    • 0001555566 scopus 로고
    • Prepared using a modification of Raucher's procedure see: S. Raucher, and B.L. Bray J. Org. Chem. 52 1987 2332 and also Ref. 7a
    • (1987) J. Org. Chem. , vol.52 , pp. 2332
    • Raucher, S.1    Bray, B.L.2
  • 80
    • 0001170349 scopus 로고
    • 5) generated in this sequence is presumably also able to participate in a [2+2+1] reaction with 5 affording the cyclopentadienone iii, which evidently suffers reduction under the reaction conditions to cyclopentenone 16. The moderate yield observed in the key benzannulation step (31%) presumably reflects the fine balance between the desired transformation and a miriad of other possible pathways in this case. For related group 6-mediated [2+2+1] cycloadditions of eneynes see: Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 1154
    • Hoye, T.R.1    Suriano, J.A.2
  • 81
    • 0035479530 scopus 로고    scopus 로고
    • The [2+2+1] cycloaddition of ynol ethers with alkynes also has literature precedent (Imbriglio, J. E.; Rainier, J. D. Tetrahedron Lett. 2001, 42, 6987).
    • (2001) Tetrahedron Lett. , vol.42 , pp. 6987
    • Imbriglio, J.E.1    Rainier, J.D.2
  • 82
    • 0031013620 scopus 로고    scopus 로고
    • Herndon (Herndon, J. W.; Patel, P. P. Tetrahedron Lett. 1997, 38, 59) has reported the reduction of cyclopentadienones by 'Cr(0)' in the presence of a proton source.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 59
    • Herndon, J.W.1    Patel, P.P.2
  • 83
    • 0001451520 scopus 로고
    • The formation of cyclopentenones during Dötz reactions also has literature precedent (Yamashita, A.; Toy, A.; Watt, W.; Muchmore, C. R. Tetrahedron Lett. 1988, 29, 3403)
    • 5) generated in this sequence is presumably also able to participate in a [2+2+1] reaction with 5 affording the cyclopentadienone iii, which evidently suffers reduction under the reaction conditions to cyclopentenone 16. The moderate yield observed in the key benzannulation step (31%) presumably reflects the fine balance between the desired transformation and a miriad of other possible pathways in this case. For related group 6-mediated [2+2+1] cycloadditions of eneynes see: Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. The [2+2+1] cycloaddition of ynol ethers with alkynes also has literature precedent (Imbriglio, J. E.; Rainier, J. D. Tetrahedron Lett. 2001, 42, 6987). Herndon (Herndon, J. W.; Patel, P. P. Tetrahedron Lett. 1997, 38, 59) has reported the reduction of cyclopentadienones by 'Cr(0)' in the presence of a proton source. The formation of cyclopentenones during Dötz reactions also has literature precedent (Yamashita, A.; Toy, A.; Watt, W.; Muchmore, C. R. Tetrahedron Lett. 1988, 29, 3403).
    • (1988) Tetrahedron Lett. , vol.29 , pp. 3403
    • Yamashita, A.1    Toy, A.2    Watt, W.3    Muchmore, C.R.4
  • 90
    • 0035835953 scopus 로고    scopus 로고
    • For a review of Brook-type rearrangements see: W.H. Moser Tetrahedron 57 2001 2065
    • (2001) Tetrahedron , vol.57 , pp. 2065
    • Moser, W.H.1
  • 93
    • 33644840532 scopus 로고    scopus 로고
    • note
    • 8Cr requires C 46.68%, H 3.36%.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.