Synthetic studies on lemonomycin: construction of the tetracyclic core

被引：6
|
作者：
Jimenez-Somarribas, Alberto [1 ]
Williams, Robert M. [1 ,2 ]
机构：
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
[2] Univ Colorado, Ctr Canc, Aurora, CO 80045 USA
来源：
TETRAHEDRON | 2013年 / 69卷 / 35期
基金：
美国国家卫生研究院;
关键词：
(-)-Lemonomycin; Tetrahydroisoquinoline antitumor antibiotics; Pictet-Spengler reaction; 3+2] Dipolar cycloaddition; THIAZOLYL PEPTIDE ANTIBIOTICS; STRUCTURAL ELUCIDATION; ASYMMETRIC-SYNTHESIS; (-)-LEMONOMYCIN; OXIDATION; FERMENTATION; SUPERACIDS; FRAMEWORK; TAXONOMY; ANALOG;
D O I：
10.1016/j.tet.2013.05.009
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A substrate-induced stereocontrol strategy was used to gain access to the tetracyclic core of (-)-lemonomycin. An advanced intermediate was prepared from a known substituted tyrosinol through a 16-step sequence, which involved a Pictet-Spengler reaction, a [3+2] dipolar cycloaddition and an enamide hydrogenation. (C) 2013 Published by Elsevier Ltd.
引用
收藏
页码：7505 / 7512
页数：8
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