2016
DOI: 10.1039/c5ob02680f
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A convenient approach to an advanced intermediate toward the naturally occurring, bioactive 6-substituted 5-hydroxy-4-aryl-1H-quinolin-2-ones

Abstract: 5-Hydroxy-4-aryl-3,4-dihydro-1H-quinolin-2-ones are a small family of natural products isolated from fungal strains of Penicillium and Aspergillus. Most of its members, which are insecticides and anthelmintics, carry an isoprenoid C-6 side chain. The synthesis of a 6-propenyl-substituted advanced intermediate for the total synthesis of these natural products is presented in this paper. This was achieved through the stereoselective construction of a β,β-diarylacrylate derivative from 6-nitrosalicylaldehyde, usi… Show more

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Cited by 20 publications
(8 citation statements)
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“…2a ) 20 25 . Simonetti and co-workers developed a convenient way to install 6-propenyl side chain by Claisen rearrangement of 5- O -allyl in the heterocycle 21 . Similar reaction was also used in the construction of unsaturated pyran fragments in yaequinolones J1 and J2 26 by Vece and co-workers 22 , as well as the synthesis of aniduquinolone C and peniprequinolone by Christmann’s group 23 .…”
Section: Introductionmentioning
confidence: 99%
“…2a ) 20 25 . Simonetti and co-workers developed a convenient way to install 6-propenyl side chain by Claisen rearrangement of 5- O -allyl in the heterocycle 21 . Similar reaction was also used in the construction of unsaturated pyran fragments in yaequinolones J1 and J2 26 by Vece and co-workers 22 , as well as the synthesis of aniduquinolone C and peniprequinolone by Christmann’s group 23 .…”
Section: Introductionmentioning
confidence: 99%
“…2c ). For example, reduction of the NO 2 group in 4b followed by an intramolecular ester-to-amide exchange could give lactam 4b-1 that bears a quinolone core widely found in natural products and bioactive molecules 35 . The alkene in allylic alcohol 4b could be easily converted to epoxide 4b-2 in 87% yield with excellent stereo-selectivity (only one diastereoisomer was obtained).…”
Section: Resultsmentioning
confidence: 99%
“…Quinolinones 6g and 6h underwent Claisen rearrangement at 150 °C in 1,2-dichlorobenzene for 10 hours to give 12a and 12b in 71% and 63% yield, respectively (Scheme 3). 22 At higher temperature and prolonged reaction time, elimination of the tertiary alcohol was observed. Olefin metathesis of 12a using Umicore M71SIMes as catalyst and an excess of 2-methylbut-2ene gave (±)-aniduquinolone C (13a) 21 in 81% yield, whereas (±)-peniprequinolone (13b) 20 was obtained in 80% yield starting from 12b.…”
Section: Scheme 2 Intramolecular Aldolizationmentioning
confidence: 98%