奥维诺醇6,14-桥的官能化。2. 18-和19-羟基取代的酒石醇的制备及其与苄基溴的反应。
Functionalization of the 6,14-bridge of the orvinols. 2. Preparation of 18- and 19-hydroxyl-substituted thevinols and their treatment with benzyl bromide.
作者信息
Wu Huifang, Bernard Denzil, Chen Weibin, Strahan Gary D, Deschamps Jeffrey R, Parrish Damon A, Lewis John W, MacKerell Alexander D, Coop Andrew
机构信息
Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, 20 Penn Street, Room 637, Baltimore, Maryland 21201, USA.
出版信息
J Org Chem. 2005 Mar 4;70(5):1907-10. doi: 10.1021/jo048388u.
The etheno bridge of a thevinone was treated with BH3 and H2O2 to give both the 18- and 19-hydroxyl- substituted thevinols. Selective benzylation of the primary 20-hydroxyl over the 19-hydroxyl was successful; however, benzylation of the 18-hydroxylated product led to a reaction at the more hindered alcohol. Thus, the 6,14-bridge of the Diels-Alder products of thebaine can be hydroxylated, which opens up these positions for further chemical manipulation.
将蒂夫诺酮的乙烯基桥用硼氢化钠和过氧化氢处理，得到18-和19-羟基取代的蒂夫诺醇。在伯羟基20-羟基上相对于19-羟基的选择性苄基化是成功的；然而，18-羟基化产物的苄基化导致在空间位阻更大的醇处发生反应。因此，蒂巴因的狄尔斯-阿尔德产物的6,14-桥可以被羟基化，这为进一步的化学操作开辟了这些位置。
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