1985
DOI: 10.1021/jo00210a030
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The structure of the glycolipid components of the aridicin antibiotic complex

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Cited by 22 publications
(8 citation statements)
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“…Homolycorine was isolated from Narcissus confusus. The physical data of the isolated compound (m.p., [a]o, UV, IR, ELMS, I H NMR, J3C NMR and CD) were in accordance with those reported previously (Jeffs et al, 1985;Bastida et al, 1987;Wagner et al, 1996). Crystals for X-ray analysis were obtained by evaporation of water from an aqueous solution containing HCI.…”
Section: Methodssupporting
confidence: 89%
“…Homolycorine was isolated from Narcissus confusus. The physical data of the isolated compound (m.p., [a]o, UV, IR, ELMS, I H NMR, J3C NMR and CD) were in accordance with those reported previously (Jeffs et al, 1985;Bastida et al, 1987;Wagner et al, 1996). Crystals for X-ray analysis were obtained by evaporation of water from an aqueous solution containing HCI.…”
Section: Methodssupporting
confidence: 89%
“…[41][42][43] Employing similar standard methods methyl 3,4-di-O-acetyl-2-deoxy-a-d-glucopyranoside (16) was synthesized. [39,[44][45][46][47] Both compounds were subjected to the same reaction conditions, which through displacement of the mesylate and oxidation of the corresponding sulfonyl acetate lead to compounds 17 and 18 in a yield of 79 and 60 %, respectively, over three steps. Generation of the sulfonyl chloride under standard conditions, [48] followed by coupling to [6-(2,5-dihydro-1H-pyrrol-1-yl)-6-oxohexyl]amine (24) [31] and dihydroxylation of the pyrroline double bond afforded compounds 19 and 20 (24 and 46 % yield) in three steps.…”
Section: Resultsmentioning
confidence: 99%
“…The following compound was synthesized starting from www.chemeurj.org methyl 2-deoxy-2-[(benzyloxycarbonyl)amino]-a-d-glucopyranoside according to known procedures [39,[44][45][46][47] …”
Section: Methyl 34-di-o-acetyl-2-deoxy-2-[(benzyloxycarbonyl)amino]-mentioning
confidence: 99%
“…Glacial acetic (50 μL) acid was added to the product-containing fractions, followed by drying under vacuum to give the title compound 6 S - 2 H-4 as colorless oil (10.4 mg, 0.041 mmol, 55%), whose non-deuteriated isotopomer was previously reported as the free base. 29 [α]normalD23=+152.3 ( c = 0.1, water). 1 H NMR (600 MHz, D 2 O): δ = 4.85 (d, J 1-2 = 3.7 Hz, 1H, H1); 3.86 (t, J 3-2 = J 3-4 = 9.7 Hz, 1H, H3); 3.60 (d, J 6-5 = 5.1 Hz, 1H, H6); 3.53 (dd, J 5-4 = 9.8 Hz, J 5-6 = 5.1 Hz, 1H, H5); 3.31 (t, J 4-3 = J4-5 = 9.7 Hz, 1H, H4); 3.28 (s, 3H, -OCH 3 ); 3.16 (dd, J 2-1 = 3.7 Hz, J 2-3 = 9.9 Hz, 1H, H2).…”
Section: Methodsmentioning
confidence: 99%