Synthetic method of marine natural product namely (R, Z)-24-methyl-25-carbon-16-butylene-2,4-diyne-1,6-diol and enantiomer thereof

The invention relates to a synthetic method of a marine natural product namely (R, Z)-24-methyl-25-carbon-16-butylene-2,4-diyne-1,6-diol and an enantiomer thereof, and belongs to the field of chemical synthesis. The synthetic method comprises the following steps: firstly, preparing long chain alkyl...

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Hauptverfasser: LI SHUONING, ZHONG JIANGCHUN, LIU SHIKUO, LI MINYAN, ZHENG BING, LIU FEIPENG, BIAN QINGHUA
Format: Patent
Sprache:eng
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Zusammenfassung:The invention relates to a synthetic method of a marine natural product namely (R, Z)-24-methyl-25-carbon-16-butylene-2,4-diyne-1,6-diol and an enantiomer thereof, and belongs to the field of chemical synthesis. The synthetic method comprises the following steps: firstly, preparing long chain alkyl iodide by using a series of simple reactions including bromination, oxidation, esterification, reduction and the like; and then, performing multiple steps of reactions including coupling, dislocation, oxidation, selective reduction, asymmetric alkynylation addition, esterification, hydrolysis and the like by taking propargyl alcohol and the long chain alkyl iodide as starting materials to synthesize the marine natural product namely (R, Z)-24-methyl-25-carbon-16-butylene-2,4-diyne-1,6-diol and the enantiomer thereof, wherein the key step is that trimethylsilylacetylene and alkynal are subjected to asymmetric addition reaction to generate alkynol segments with high optical purity by one step. The synthetic method provided by the invention reports the synthesis of the natural product of the type for the first time, and has the characteristics of simple and convenient steps, relatively high total yield, good product stereoselectivity and the like, and the optical purity of each of the two types of synthesized products is more than 99%ee.