Convenient Synthesis of Fragment E of Antibiotic, Nosiheptide

Construction of Substituted N‐Hydroxyindoles: Synthesis of a Nocathiacin I Model System

“…The required starting material for these studies, nitro ketoester 6 , was readily prepared by standard chemistry2c, 5, 6 in two steps from aromatic compound 4 via intermediate 5 (Scheme ). Schemes and summarize the initial results of this study and demonstrate the feasibility of this plan under two different sets of experimental conditions.…”

Totalsynthese von Nosiheptid

“…[36] Tristhiazolylpyridin 42, [37] (57), [36] 1,2-(Z)-Methoxycarbonyl-1,3-bis(trimethyl-silyloxy)-1,3-butadien (65), [37] 2-Nitro-6-(2'-tetrahydropyranyloxymethyl)phenyl-brenztrauben-säureethylester (75), [153] 3-Hydrox-ypyridin-5,6-bis(trideutero-methoxycarbonyl)-2-carbon-säuremethylester (97-d 6 ), [241] 131 3-Hydroxypicolinsäuremethylester (100), [278] L-Boc-Thr(TBS)-OH (140), [201] L-FmocThr(TBS)-OH (143), [202] 2'-Bromacetyl-pyridin (161), [219] 6-Brom-3-hydroxypicolinsäure-methyl-ester (204), [267] 4-(Tributyl-stannyl)-1-trityl-1H-imidazol (217), [269] 4,6-Dibrom-3-hydroxy-picolinsäure-diemethylester (228), [278] Dess-Martin-Periodinan, [312] 3-Hydroxypyridin-2,5,6-tricarbonsäure-trimethylester, [37] 3-Meth-oxypicolinsäuremethyl-ester(240) [308] Indol-2-boron-säurepinakolester, [313] Indol-3-boronsäurepinakol-ester, [314] 1H-Pyrrol-3-boronsäure-pinakolester, [315] 1-(Tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-boronsäurepinakol-ester, [268] Pyrazol-4-boronsäurepinakolester, [314] (R)-2-Azido-3-(tritylthio)-propansäureallyl-ester, [37] PyDOP. [225] Dichlormethan [316] die Sporen wurden anschließend geerntet und in Glycerol gelagert.…”

Catalytic Asymmetric Baeyer–Villiger Oxidation in Water by Using PtII Catalysts and Hydrogen Peroxide: Supramolecular Control of Enantioselectivity

“…Synthetic routes to the nosiheptide indole 116 (X=H) have been developed based on an intramolecular Heck reaction of an iodoaniline derivative 115 ,93a or a classical Reissert synthesis of nitrotoluene 117 to give a 4‐substituted indole‐2‐carboxylate 118 . Following hydrolysis to the corresponding carboxylic acid ( 118 , R 2 =H), the 3‐position was methylated (Scheme ) 93b. We used the thermolysis of readily available azidocinnamates 119 to access the same 2,4‐disubstituted indole 118 , followed by introduction of the C‐3 substituent by formylation.…”