54088-99-2Relevant articles and documents
Total Syntheses of (R)-Strongylodiols C and D
Liu, Feipeng,Zhong, Jiangchun,Li, Shuoning,Li, Minyan,Wu, Lin,Wang, Qian,Mao, Jianyou,Liu, Shikuo,Zheng, Bing,Wang, Min,Bian, Qinghua
, p. 244 - 247 (2016/02/05)
The first total syntheses of two marine natural products, (R)-strongylodiols C and D, with 99% ee were achieved. The key steps of the strategy include the zipper reaction of an alkyne, the asymmetric alkynylation of an unsaturated aliphatic aldehyde catalyzed with Trost's ProPhenol ligand, and the Cadiot-Chodkiewicz cross-coupling reaction of a chiral propargylic alcohol with a bromoalkyne.
A marine natural product (R, Z) - 24-methyl-twenty-five carbon -16-butene -2,4-diyne -1,6-diol and its antimer synthesis method
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, (2020/05/06)
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.
Coupling Reaction of Grignard Reagents with α,ω-Dibromoalkanes in the Presence of Copper(I) Bromide-HMPA: Preparation of α,ω-Bis(vinylaryl)alkanes
Nishimura, Jun,Yamada, Noriyuki,Horiuchi, Yuzuru,Ueda, Eiji,Ohbayashi, Akihiro,Oku, Akira
, p. 2035 - 2037 (2007/10/02)
The coupling reaction of Grignard reagents with α,ω-dibromoalkanes took place smoothly in THF/HMPA (12:1) in the presence of a catalytic amount of copper(I) bromide and gave the products in 60-100 percent yields.Several α,ω-bis(vinylaryl)alkanes were prepared in reasonable yields by the application of this reaction.
