Synthesis of γ-Monofluorinated Goniothalamin Analogues via Regio- and Stereoselective Ring-Opening Hydrofluorination of Epoxide
Synthesis of γ-Monofluorinated Goniothalamin Analogues via Regio- and Stereoselective Ring-Opening Hydrofluorination of Epoxide
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DOI：
10.1021/jo200611w
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发表时间：
2011-08-19
影响因子：
3.6
通讯作者：
Qing, Feng-Ling
中科院分区：
文献类型：
--
作者：
Chen, Jun-Ling;Zheng, Feng;Qing, Feng-Ling
本文报道了一种立体选择性合成具有生物学意义的γ-单氟化角柳胺类似物2a的方法。合成的特征包括化合物10的未保护的羟基丙炔基部分被Red-Al区域选择性还原，烯丙醇11的不对称Sharpless环氧化，以及区域和立体选择性的环-用Et 3 N中心点3 HF在高ee和dr下打开羟基丙炔基环氧化物14的氢化。γ-单氟化α，β-不饱和δ-内酯。
A stereoselective synthesis of the biologically interesting gamma-monofluorinated goniothalamin analogue 2a was described. The features of the synthesis included regioselective reduction of the unprotected hydroxypropynyl moiety of compound 10 by Red-Al, asymmetric Sharpless epoxidation of allyl alcohol 11, and regio- and stereoselective ring-opening hydrofluorination of the hydroxypropynyl epoxide 14 with Et3N center dot 3HF in high ee and dr. The chiral hydroxypropynyl fluorohydrin 15 was used as a valuable building block for preparation of a range of gamma-monofluorinated alpha,beta-unsaturated delta-lactones.