Synthesis and biological evaluation of deoxypreussomerin A and palmarumycin CP1 and related naphthoquinone spiroketals

被引：47

作者：

Wipf, P ^{[1
]}

Jung, JK

Rodríguez, S

Lazo, JS

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

[2] Univ Pittsburgh, Dept Pharmacol, Pittsburgh, PA 15260 USA

来源：

TETRAHEDRON | 2001年 / 57卷 / 02期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

spirocyclization; naphthoquinone; palmarumycin; deoxypreussomerin; total synthesis; polymer-bound reagent; iodobenzenediacetate; phenol oxidation; cytotoxicity; breast cancer cell line;

D O I：

10.1016/S0040-4020(00)00936-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidative cyclization of bis-hydroxynaphthyl ethers allows concise total syntheses of palmarumycin CP1 and deoxypreussomerin A in 8-9 steps and 15-35% overall yield from 5-hydroxy-8-methoxy-1-tetralone (8). Polymer-bound triphenyl phosphine was found to be a superior reagent for the rapid preparation of a small library of palmarumycin analogs. Preliminary biological evaluation of naphthoquinone spiroketals against MCF-7 and MDA-MB-231 human breast cancer cells revealed several low-micromolar growth inhibitors. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：283 / 296

页数：14

共 35 条

[1] Total syntheses of palmarumycins CP1 and CP2 and CJ-12,371:: novel spiro-ketal fungal metabolites [J].