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Volumn 70, Issue 16, 2005, Pages 6339-6345

Three-component one-pot total syntheses of glyantrypine, fumiquinazoline F, and fiscalin B promoted by microwave irradiation

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BIOCHEMISTRY; IRRADIATION; MICROWAVES; REACTION KINETICS; SCAFFOLDS; SYNTHESIS (CHEMICAL);

EID: 23044468194     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0508043     Document Type: Article
Times cited : (99)

References (52)
  • 1
    • 7744242263 scopus 로고    scopus 로고
    • For recent reviews on quinazoline alkaloids, see: (a) Michael, J. P. Nat. Prod. Rep. 2004, 21, 650.
    • (2004) Nat. Prod. Rep. , vol.21 , pp. 650
    • Michael, J.P.1
  • 30
    • 33745743691 scopus 로고    scopus 로고
    • For a recent review of microwave-assisted organic synthesis, see: Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6251.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 6251
    • Kappe, C.O.1
  • 33
    • 84890597202 scopus 로고    scopus 로고
    • Wiley-VCH: Weinheim, Germany
    • For multicomponent reactions, see: (a) Multicomponent Reactions; Zhu, J., Bienaymé, H., Eds.; Wiley-VCH: Weinheim, Germany, 2005.
    • (2005) Multicomponent Reactions
    • Zhu, J.1    Bienaymé, H.2
  • 44
    • 33544457548 scopus 로고    scopus 로고
    • note
    • The reaction utilizing Boc-amino acids provided reaction mixtures with fewer side products.
  • 45
    • 33544469851 scopus 로고    scopus 로고
    • note
    • In all cases where we have used conventional heating to generate intermediates corresponding to 19, microwave heating could generate the same products, albeit in lower yields.
  • 46
    • 33544456990 scopus 로고    scopus 로고
    • note
    • As a comparison, a control reaction was carried out in a sealed tube under conventional heating in an oil bath at 210 °C (the minimal temperature required for the reaction to proceed) for 15 min. The product 2 was formed, but the crude reaction mixture was more complex with multiple side products and fully racemized products (LC/MS, ELSD = 60%, ee = 0%) as compared with the microwave conditions which provided the product in higher yield with minimal side reactions and with much less enantiomeric erosion (LC/MS, ELSD = 75%, ee = 70%). Additionally, the conventional heating conditions (sealed tube) are not practical for parallel synthesis of analogue libraries of the natural products, which is an effort that we are pursuing.
  • 47
    • 33544469633 scopus 로고    scopus 로고
    • note
    • The synthesis of 3 was also achieved with the use of D-tryptophan methylester, resulting in an identical yield and optical purity under the same microwave conditions as those used for D-tryptophan methylester hydrochloride (10d).
  • 48
    • 33544457738 scopus 로고    scopus 로고
    • note
    • 13C NMR relative to enantiomerically pure 3.
  • 49
    • 33544463421 scopus 로고    scopus 로고
    • note
    • 1H NMR is identical with fumiquinazoline G in ref 9b. The chiral SFC/MS analysis confirmed that it is a racemate of 4.
  • 50
    • 33544456687 scopus 로고    scopus 로고
    • note
    • 3)}. See the Experimental Section for details.
  • 51
    • 0035956415 scopus 로고    scopus 로고
    • See ref 10b
    • Steric hindrance is an important factor in unsuccessful quinazolinone ring formation in Fiscalin B total synthesis. See the discussion in: Buenadicha, F. L.; Avendaño, C.; Söllhuber, M. Tetrahedron: Asymmetry 2001, 12, 3019. See ref 10b.
    • (2001) Tetrahedron: Asymmetry , vol.12 , pp. 3019
    • Buenadicha, F.L.1    Avendaño, C.2    Söllhuber, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.