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Volumn 69, Issue 10, 2004, Pages 3368-3374

Total Synthesis and Preliminary Biological Evaluation of cis-Solamin Isomers

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; OXIDATION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); TOXICITY;

EID: 2442682076     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049909g     Document Type: Article
Times cited : (62)

References (85)
  • 8
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    • For reviews of acetogenin synthesis up to 1998, see refs 1 and: (a) Hoppe, R.; Scharf, H. D. Synthesis 1995, 1447-1464.
    • (1995) Synthesis , pp. 1447-1464
    • Hoppe, R.1    Scharf, H.D.2
  • 9
    • 77957030220 scopus 로고    scopus 로고
    • Atta-ur-Rahman, Ed.; Elsevier Science B. V.: Amsterdam
    • (b) Figadère, B.; Cavé, A. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science B. V.: Amsterdam, 1996; Vol. 18, pp 193-227.
    • (1996) Studies in Natural Products Chemistry , vol.18 , pp. 193-227
    • Figadère, B.1    Cavé, A.2
  • 34
    • 37049080609 scopus 로고
    • For examples of the stereoselective synthesis of cis-mono-THF Annonaceous 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.
    • (1994) J. Chem. Soc., -Perkin Trans. 1 , pp. 1975-1981
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    • (d) For a preliminary communication of part of this work: Cecil, A. R. L.; Brown, R. C. D. Org. Lett. 2002, 4, 3715-3718.
    • (2002) Org. Lett. , vol.4 , pp. 3715-3718
    • Cecil, A.R.L.1    Brown, R.C.D.2
  • 38
    • 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
  • 53
  • 60
    • 0001314709 scopus 로고
    • For related oxidative cyclizations of hydroxy olefins by metal-oxo species, see refs 41, 6c, and: (a) 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
  • 74
    • 2442709299 scopus 로고    scopus 로고
    • note
    • The stereochemistry of the major diastereoisomer was assigned on the basis of literature precedent for the oxidative cyclization of closely related substrates (see ref 10f,i).
  • 75
    • 2442701884 scopus 로고    scopus 로고
    • Commemorative Issue in Honor of Prof. B. S. Thyagarajan, ms. BT-336D (http://www.Arkat-usa.org/ark/journal/Volume2/Part3/Thyagarajan/BT-335D/336d. pdf).
    • 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-335D/336d. pdf).
    • (2001) Arkivoc , Issue.PART XI
    • Cecil, A.R.L.1    Brown, R.C.D.2
  • 77
    • 2442639282 scopus 로고    scopus 로고
    • note
    • major signals, leading us to initially report a higher value of 10:1. The dr value of 6:1 was confirmed from the isolated yields of 5 and 16.
  • 78
    • 2442686980 scopus 로고    scopus 로고
    • note
    • The diastereofacial selectivity observed for the oxidative cyclization of enantiomerically enriched N-enoyl oxazolidinones was previously explained by dipolar organization of the substrate (see ref 10f).
  • 79
    • 0012321996 scopus 로고    scopus 로고
    • Schmalz, H.-G., Ed.; Wiley-VCH: Weinheim
    • Reiser, O. In Organic Synthesis Highlights IV; Schmalz, H.-G., Ed.; Wiley-VCH: Weinheim, 2000; pp 11-16.
    • (2000) Organic Synthesis Highlights IV , pp. 11-16
    • Reiser, O.1
  • 80
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    • note
    • 13C NMR spectra.
  • 82
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    • note
    • 3).
  • 83
    • 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
  • 84
    • 2442665611 scopus 로고    scopus 로고
    • note
    • Each of the four isomers (1, ent-1, 2, and ent-2) gave a separate and single peak on a Chiral CD-Ph HPLC column, eluting with i-PrOH/hexane (15:85). Retention times: 1 (14.5 min), 2 (17.3 min), ent-1 (18.7 min), ent-2 (15.7 min). See the Supporting Information for an HPLC trace for a mixed sample of 1 and 2.


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