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Cited by 68 publications
(43 citation statements)
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“…Carboxylic acids 1b-1f used are commercially available, although 1a and 1e were readily prepared on gram-scale from indole-3-carbonitrile 14 and indole 23 respectively by basic alkylation and hydrolysis of methyl esters. HOTT though commercially available, was accessed using the literature procedure, 16 which in our hands yielded almost 10 g of HOTT in 65% yield.…”
Section: Methodsmentioning
confidence: 99%
See 1 more Smart Citation
“…Carboxylic acids 1b-1f used are commercially available, although 1a and 1e were readily prepared on gram-scale from indole-3-carbonitrile 14 and indole 23 respectively by basic alkylation and hydrolysis of methyl esters. HOTT though commercially available, was accessed using the literature procedure, 16 which in our hands yielded almost 10 g of HOTT in 65% yield.…”
Section: Methodsmentioning
confidence: 99%
“…and 1b) into Barton esters using Garner's HOTT (S-(1-oxido-2-pyridinyl)-1,1,3,3-tetramethyl thiouronium hexafluorophosphate) 16 in the absence of light (Scheme 1). HOTT is a useful coupling reagent for forming labile Barton esters from hindered or difficult carboxylic acids.…”
Section: Scheme 1 One-pot Initiator-free Tandem Reactions With 3-submentioning
confidence: 99%
“…The radicals were generated via the combined thermal and photochemical decomposition of Barton ester {pyridine-2-thione-N-oxycarbonyl (PTOC) or Oacyl thiohydroxamate} 2 intermediates formed from carboxylic acids using the Garner coupling reagent, HOTT (S-(1-oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium hexafluorophosphate). 3 All six-membered radical cyclizations were high yielding (~80%), but the more challenging five and seven-membered cyclizations were found to give lower yields (<50%), with the exception of (i) the five-membered alkyl and cyclopropyl radical cyclizations onto indole-3-carbonitrile, which occurred in 75 and 78% yields respectively, and (ii) the seven-membered alkyl radical cyclization onto indole-3-carbonitrile gave a 61% yield. The structures of the indole fivemembered cyclization adducts correspond to the skeleton of Moody's cyclopropamitosene, a hypoxic tumor cell selective cytotoxin, 4 which was previously prepared using intramolecular 1,3- The inherent light and hydrolytic sensitivity of the required Barton esters led to difficulty in the clean isolation of these intermediates.…”
Section: Introductionmentioning
confidence: 99%
“…Therefore, after hydrolysis of ester group, the oxidative decarboxylation of carboxylic acid 11 was examined under various conditions. The desired compound 12 was obtained in good yield when Garner et al's procedure 13) was applied. Reduction of the carbonyl group of 12 with metallic Li in liquid ammonia in the presence of MeOH gave 13 quantitatively.…”
mentioning
confidence: 99%
“…Reduction of the carbonyl group of 12 with metallic Li in liquid ammonia in the presence of MeOH gave 13 quantitatively. Thus a total synthesis of the racemate of culmorin (13) was accomplished in 46% overall yield in 11 steps from the known compound 5. 14,15) …”
mentioning
confidence: 99%