Exceedingly Efficient Synthesis of (±)-Grandifloracin and Acylated Analogues

被引：21

作者：

Bergner, Magnus ^{[1
]}

Duquette, Douglas C. ^{[1
]}

Chio, Linda ^{[1
]}

Stoltz, Brian M. ^{[1
]}

机构：

[1] CALTECH, Warren & Katharine Schlinger Lab Chem & Chem Engn, Div Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 12期

基金：

美国国家科学基金会;

关键词：

ARENE OXIDATION-PRODUCT; PANCREATIC-CANCER; PERIODATE OXIDATION; CYTOTOXIC ACTIVITY; (+)-GRANDIFLORACIN; DEAROMATIZATION; GEMCITABINE; MECHANISM; PHENOLS; CELLS;

D O I：

10.1021/acs.orglett.5b01292

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient regio- and stereoselective total synthesis of (+/-)-grandifloracin via a tandem dearomative epoxidation/spontaneous Diels-Alder cyclodimerization from salicylic acid in only four steps is reported. The synthetic route allows for late-stage diversification of the core structure to give ready access to analogues of this promising agent against pancreatic cancer.

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收藏

页码：3008 / 3010

页数：3

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