Asymmetric Synthesis of Fortucine and Reassignment of Its Absolute Configuration

被引：34

作者：

Beaulieu, Marc-Andre ^{[1
]}

Ottenwaelder, Xavier ^{[2
]}

Canesi, Sylvain ^{[1
]}

机构：

[1] Univ Quebec, Dept Chim, Lab Methodol & Synth Prod Nat, Montreal, PQ H3C 3P8, Canada

[2] Concordia Univ, Dept Chem & Biochem, Montreal, PQ H4B 1R6, Canada

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 25期

基金：

加拿大自然科学与工程研究理事会; 加拿大创新基金会;

关键词：

aromatic ring umpolung; hypervalent iodine; natural products; oxidation; total synthesis; HYPERVALENT IODINE REAGENT; PINACOL TANDEM PROCESS; CARBON BOND FORMATION; PHENOL DEAROMATIZATION; AMARYLLIDACEAE; ALKALOIDS; OXIDATION; GENERATION; CHEMISTRY; LYCORINE;

D O I：

10.1002/chem.201402323

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convergent and enantioselective synthesis of fortucine was achieved from the starting materials tyrosine methyl ester and 3-hydroxy-4-methoxybenzaldehyde. The synthesis is based on two key steps mediated by a hypervalent iodine reagent. This work has enabled us to reassign the absolute configuration of the natural product reported in the literature.

引用

页码：7581 / 7584

页数：4

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