Design and synthesis of terpene based englerin A mimics using chromium oxide mediated remote CH2 oxidation

被引：14

作者：

Acerson, Mark J. ^{[1
]}

Bingham, Brian S. ^{[1
]}

Allred, Curtis A. ^{[1
]}

Andrus, Merritt B. ^{[1
]}

机构：

[1] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 23期

关键词：

C-H activation; CH2; oxidation; Chromium oxide; Terpene; Englerin A; Cancer; ALLYLIC OXIDATION; METHYL(TRIFLUOROMETHYL)DIOXIRANE; OLEFINS; ANALOGS;

D O I：

10.1016/j.tetlet.2015.02.071

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Terpene based mimics of the anti-cancer agent (-)-englerin A have been designed and produced from (+)- and (-)-bornyl acetate and (+)-fenchol. A key remote CH2 oxidation reaction was developed using chromium(VI) oxide in acetic acid (115 degrees C) added in two portions to access keto-acetate intermediates in good yields (40-70%). Other known C-H activation conditions for this methylene oxidation were ineffective. Standard acylation steps installed the glycolate and cinnamate esters leading to the desired mimics. Preliminary cell testing with renal cancer cells show less potent activity compared to englerin A. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：3277 / 3280

页数：4