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SM ISO690:2012 POGREBNOI, Vsevolod, SUCMAN, Natalia, MAKAEV, Fliur. The spirocyclopropane with fragments of dehydroabietic acid and aminooxindole. In: New frontiers in natural product chemistry, Ed. 7, 12-13 octombrie 2023, Chișinău. Chișinău, Republica Moldova: Tipografia "Artpoligraf", 2023, Ediția 7, p. 22. DOI: https://doi.org/10.19261/nfnpc.2023.ab15 |
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New frontiers in natural product chemistry Ediția 7, 2023 |
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Conferința " New frontiers in natural product chemistry." 7, Chișinău, Moldova, 12-13 octombrie 2023 | |||||||
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DOI:https://doi.org/10.19261/nfnpc.2023.ab15 | |||||||
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The abstract presents the synthesis of new highly functionalized spirocyclopropane with the fragment of natural compound – dehydroabietic acid 1 (DAK), which can be potentially active against some diseases.It is a known that spirocyclopropanes have anti-HIV activity [1]. From the other side there are a lot of natural and synthetical oxindoles with various biological activities [2]. And the last fact – that the high optical purity and the molecular structure of tricyclic diterpenoid 1 make it an attractive object for studying new various properties, such as the synthesis of new derivatives with the natural skeleton preservation [3]. Firstly, our approach was to isolate the DAK from natural sources and to transform into chloride 2. The next stage was the obtaining of 5-aminooxindole 6, which started from isatine 4, according to a known method [4]. The sequential three-stage synthesis of oxindole 5 [5] followed by classical reduction with hydrogen and 5 mol% of palladium on activated carbon [6] succeeded with 98% yield. And the final stage was the reaction of aminooxindole 6 with chloride 2 in dry chloroform, using as acceptor the excess Et3N. According to NMR spectrum, the desired product 7 is the mixture of diastereomers in ratio 1:1. |
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