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Volumn , Issue 4, 2003, Pages 522-526

A new convergent approach to biphenomycin antibiotics

Author keywords

Antibiotics; Asymmetric synthesis; Biphenomycins; Cyclopeptides; Stille coupling

Indexed keywords

3 (2 HYDROXYPHENYL)ALANINE; ANTIBIOTIC AGENT; BIPHENOMYCIN A; CYCLOPEPTIDE;

EID: 0037237192     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37506     Document Type: Article
Times cited : (20)

References (34)
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    • For a recent convergent synthetic approach to related cyclopeptides, see: Carbonnelle, A.-C.; Zhu, J. Org. Lett. 2000, 2, 3477.
    • (2000) Org. Lett. , vol.2 , pp. 3477
    • Carbonnelle, A.-C.1    Zhu, J.2
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    • note
    • Benzylbromide 8 was prepared from 5-iodo-salicylic acid in 40% overall yield as indicated in Scheme 6.
  • 18
    • 0012625482 scopus 로고    scopus 로고
    • note
    • +): 398.0253; Found: 398.0253.
  • 19
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    • The enantiomeric purity of 11 was determined via its Fmoc derivative by HPLC (ChiraDex®Gamma (5-μm) LiChroCART® 250 × 4 mm (Merck) MeCN-triethylamine-AcOH, 1000:7:0.5, 1 mL/min) according to Armstrong et al. to be > 98% ee. See: Tang, Y.; Zukowski, J.; Armstrong, D. W. J. Chromatogr. A 1996, 743, 261.
    • (1996) J. Chromatogr. A , vol.743 , pp. 261
    • Tang, Y.1    Zukowski, J.2    Armstrong, D.W.3
  • 20
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    • The absolute configuration of 11 was determined to be S by conversion into -o-tyrosine, whose absolute configuration has been unambiguously established. Lit.: Dugave, C. J. Org. Chem. 1995, 60, 601.
    • (1995) J. Org. Chem. , vol.60 , pp. 601
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    • note
    • In addition to 20, 21 and 22 small amounts of the respective aryl iodide homocoupling product i (1-7%) and in case of entries 1-4 product ii (3-6%), which arises from aryl transfer by the arsine, were also obtained (Figure 2).
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    • For the preparation of 23 (Figure 3), see: Herrmann, W. A.; Broßmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844; Angew. Chem. 1995, 107, 1989.
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    • (a) Louie, J.; Hartwig, J. F. Angew. Chem. Int. Ed. Engl. 1996, 35, 2359; Angew. Chem. 1996, 108, 2531.
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    • note
    • arom).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.