2007
DOI: 10.1021/jo701599g
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Copper(I)-Mediated and Microwave-Assisted Caryl−Ocarboxylic Coupling:  Synthesis of Benzopyranones and Isolamellarin Alkaloids

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Cited by 135 publications
(58 citation statements)
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“…Thasana and coworkers reported the preparation of the coumestan derivative 95 through the intramolecular lactonization, mediated by copper(I) thiophene-2-carboxylate under MW irradiation, of 2-(2-bromophenyl)-6-methoxybenzofuran-3-carboxylic acid 94 (Scheme 42) [141]. The same reaction took place employing substoichiometric CuI (0.5 equivalent), albeit in a remarkably lower yield (31%).…”
Section: Pyrone-ring Constructionmentioning
confidence: 99%
“…Thasana and coworkers reported the preparation of the coumestan derivative 95 through the intramolecular lactonization, mediated by copper(I) thiophene-2-carboxylate under MW irradiation, of 2-(2-bromophenyl)-6-methoxybenzofuran-3-carboxylic acid 94 (Scheme 42) [141]. The same reaction took place employing substoichiometric CuI (0.5 equivalent), albeit in a remarkably lower yield (31%).…”
Section: Pyrone-ring Constructionmentioning
confidence: 99%
“…The approach of Singh and Guiry [13] involves ring opening of epoxide 41 by the Grignard reagent derived from 2-(2-bromoethyl)-2-methyl-1,3-dioxolane, in the presence of CuI (10 mol%) at −78 • C, affording syn-diol 42 in 80% yield. This was treated with ZrCl 4 (10 mol%) in methanol under MW irradiation to give (1R,5S,7S)-5-methyl-7-vinyl-6,8-dioxabicyclo[3.2.1]octane (43) in 86% yield in addition to (S)-1-[(2R,6S)-6-methoxy-6-methyltetrahydro-2H-pyran-2-yl]prop-2-en-1-ol (44). Hydrogenation of 43 in the presence of a catalytic amount of Pd/C at 10 bar gave (+)-endo-brevicomin (39) in 95% yield with an enantiomeric excess (ee) of 98.5% (Scheme 19.9).…”
Section: Total Synthesis Of Various Classes Of Natural Productsmentioning
confidence: 99%
“…This was converted into a mixture of (+)-largazole (182) The lamellarins exhibit various biological activities and are potential drug candidates for the treatment of some forms of cancer and AIDS. Thasana et al [43] reported a simple and highly effective C-O carboxylic coupling reaction catalyzed by copper(I) salts to synthesize benzopyranones under MW irradiation. The synthesis of isolamellarin (193) started from 194, which was converted into the pyrrolo[2,1-a]isoquinoline carboxylic acid 195 in excellent yield.…”
Section: Total Synthesis Of Various Classes Of Alkaloidsmentioning
confidence: 99%
“…11 Furthermore, dibenzopyranones occur naturally in many food sources including citrus fruits, herbs, and vegetables. 12 There are several methods available for the synthesis of dibenzopyranones, the most common being Suzuki cross-coupling reaction followed by Lewis acid [13][14][15][16] or metal 17 mediated lactonization. More…”
Section: Introductionmentioning
confidence: 99%