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Volumn 46, Issue 38, 2005, Pages 6417-6422

Synthetic studies on thiostrepton family of peptide antibiotics: Synthesis of the dihydroquinoline portion of thiostrepton, the siomycins, and the thiopeptins

Author keywords

Dihydroquinoline; Matsumura Boekelheide rearrangement; Siomycins; Stereoselective addition; Thiostrepton

Indexed keywords

ANTIINFECTIVE AGENT; DIHYDROQUINOLINE DERIVATIVE; POLYPEPTIDE ANTIBIOTIC AGENT; SIOMYCIN A; SIOMYCIN C; SIOMYCIN D1; THIOPEPTIN; THIOPEPTIN A1B; THIOSTREPTON; TRIETHYLAMINE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

EID: 23844477342     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.121     Document Type: Article
Times cited : (13)

References (39)
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    • note
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    • note
    • Recently, a total synthesis of thiostrepton has appeared; see Refs. 5e and 5f.
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    • note
    • 10 [ α ] D 20 -79 (c 1, EtOH)].
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    • 2O with 2,6-dimethyl- and 2,4,6-trimethylpyridine produced compounds in which a methyl hydrogen was replaced by either a trifluoromethyl or a [(trifluoromethyl) sulfinyl]oxy group, see: R.W. Binkley, and M.G. Ambrose J. Org. Chem. 48 1983 1776 1777
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    • The mechanism for deoxygenation of pyridine N-oxides with alkanesulfonyl chlorides and triethylamine has been reported, see: Y. Morimoto, H. Kurihara, C. Yokoe, and T. Kinoshita Chem. Lett. 1998 829 830
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    • note
    • The enantiomeric excess was not optimized. It was determined by chiral HPLC analysis (Daicel Chiralcel OD column, 4.6 x 250 mm, 90:10 hexane-IPA; 1 mL/min, 254 nm, t = 20.6 min; enantiomer of 19, t = 30.8 min).
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    • note
    • Recrystallization of 21 from 1:3 dioxane-hexane twice afforded crystals suitable for X-ray crystallographic analysis. Crystallographic data for 21 have been deposited with the Cambridge Crystallographic Data Centre with number 279853.
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    • note
    • The fact that the compound 10 derived from 9 was identical with that derived from methyl ketone 21 confirmed the structure of 9 which had not been determined.
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    • note
    • This argument is supported from X-ray crystallographic analysis of 21 (Fig. 2).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.