Synthesis of (+)-Pancratistatins via Catalytic Desymmetrization of Benzene

被引：79

作者：

Hernandez, Lucas W. ^{[1
]}

Pospech, Jola ^{[1
]}

Klockner, Ulrich ^{[1
]}

Bingham, Tanner W. ^{[1
]}

Sarlah, David ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2017年 / 139卷 / 44期

基金：

美国国家科学基金会;

关键词：

RING-OPENING REACTIONS; ANTINEOPLASTIC AGENTS; ISOCARBOSTYRIL ALKALOIDS; CIS-DIHYDROXYLATION; DEAROMATIZATION; PANCRATISTATIN; AMARYLLIDACEAE; (+)-7-DEOXYPANCRATISTATIN; CONSTITUENTS; 7-DEOXYPANCRATISTATIN;

D O I：

10.1021/jacs.7b10351

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise synthesis of (+)-pancratistatin and (+)-7-deoxypancratistatin from benzene using an enantioselective, dearomative tarboarnination strategy has been achieved. This approach, in combination with the judicious choice of subsequent olefin-type difunctionalization reactions, permits rapid and controlled access to a hexasubstituted core. Finally, minimal use of intermediary steps as well as direct, late stage C-7 hydroxylation provides both natural products in six and seven operations.

引用

页码：15656 / 15659

页数：4

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