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Volumn 4, Issue 21, 2002, Pages 3715-3718

Synthesis of cis-Solamin using a permanganate-mediated oxidative cyclization

Author keywords

[No Author keywords available]

Indexed keywords

BENZETHONIUM CHLORIDE; PERMANGANATE POTASSIUM;

EID: 0037126217     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026669n     Document Type: Article
Times cited : (52)

References (55)
  • 4
    • 0029923916 scopus 로고    scopus 로고
    • For a selection of recent approaches to the total synthesis of Annonaceous acetogenins, see: (b) Hoye, T. R.; Ye, Z. J. Am. Chem. Soc. 1996, 118, 1801-1802.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1801-1802
    • Hoye, T.R.1    Ye, Z.2
  • 21
    • 37049080609 scopus 로고
    • For stereoselective syntheses of cis-mono-THF acetogenins, see the following. 15,20-Di-epi-cis-solamin: (a) Makabe, H.; Tanaka, A.; Oritani, T. J. Chem. Soc., Perkin Trans. 1 1994, 1975-1981. Muricatetrocin A: (b) Bäurle, S.; Peters, U.; Friedrich, T.; Koert, U. Eur. J. Org. Chem. 2000, 65, 2207-2217.
    • (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 1975-1981
    • Makabe, H.1    Tanaka, A.2    Oritani, T.3
  • 22
    • 0033934490 scopus 로고    scopus 로고
    • For stereoselective syntheses of cis-mono-THF acetogenins, see the following. 15,20-Di-epi-cis-solamin: (a) Makabe, H.; Tanaka, A.; Oritani, T. J. Chem. Soc., Perkin Trans. 1 1994, 1975-1981. Muricatetrocin A: (b) Bäurle, S.; Peters, U.; Friedrich, T.; Koert, U. Eur. J. Org. Chem. 2000, 65, 2207-2217.
    • (2000) Eur. J. Org. Chem. , vol.65 , pp. 2207-2217
    • Bäurle, S.1    Peters, U.2    Friedrich, T.3    Koert, U.4
  • 24
    • 0033576417 scopus 로고    scopus 로고
    • For syntheses of other acetogenins where one of the THF rings is cis-2,5-disubstituted, see the following. Jimenezin (revised structure): (a) Takahashi, S.; Maeda, K.; Hirota, S.; Nakata, T. Org. Lett. 1999, 1, 2025-2028.
    • (1999) Org. Lett. , vol.1 , pp. 2025-2028
    • Takahashi, S.1    Maeda, K.2    Hirota, S.3    Nakata, T.4
  • 40
    • 0001314709 scopus 로고
    • For related oxidative cyclizations of hydroxy olefins, see: (m) Walba, D. M.; Stoudt, G. S. Tetrahedron Lett. 1982, 23, 727-730.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 727-730
    • Walba, D.M.1    Stoudt, G.S.2
  • 48
    • 0043272233 scopus 로고    scopus 로고
    • Commemorative Issue in Honor of Prof. B. S. Thyagarajan, ms. BT-336D.
    • For the synthesis of a model compound, see: Cecil, A. R. L.; Brown, R. C. D. Arkivoc 2001, Part (xi): Commemorative Issue in Honor of Prof. B. S. Thyagarajan, ms. BT-336D. http://www.Arkat-usa.org/ark/journal/ Volume2/Part3/Thyagarajan/BT-336D/336d.pdf.
    • (2001) Arkivoc , Issue.11 PART
    • Cecil, A.R.L.1    Brown, R.C.D.2
  • 53
    • 0043272234 scopus 로고    scopus 로고
    • note
    • 13C NMR spectrum. We concluded that the new peak corresponded to a C34 epimer of 14 (ent-1). Epimerization of C34 has previously been reported to occur under basic conditions (see ref 17).
  • 54
    • 0041769131 scopus 로고    scopus 로고
    • note
    • 6 Both of our samples of 1 and 14, for which the optical rotation data are reported, gave single peaks by chiral HPLC under the conditions given above (see ref 15).
  • 55
    • 0343632337 scopus 로고    scopus 로고
    • It has previously been observed that the optical rotation value of acetogenins is largely due to the stereochemistry of the butenolide and, to a lesser extent, due to the stereochemistry of the THF diol portion: Duret, P.; Figadère. B.: Hocquemiller, R.; Cavé, A. Tetrahedron Lett. 1997, 38, 8849-8852.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 8849-8852
    • Duret, P.1    Figadère, B.2    Hocquemiller, R.3    Cavé, A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.