New approaches towards the synthesis of 1,2,3,4-tetrahydro isoquinoline-3-phosphonic acid (TicP)

被引：9

作者：

Viveros-Ceballos, Jose Luis ^{[1
]}

Matias-Valdez, Lizeth A. ^{[1
]}

Sayago, Francisco J. ^{[2
]}

Cativiela, Carlos ^{[2
]}

Ordonez, Mario ^{[1
]}

机构：

[1] Univ Autonoma Estado Morelos, Ctr Invest Quim IICBA, Av Univ 1001, Cuernavaca 62209, Morelos, Mexico

[2] Univ Zaragoza, CSIC, ISQCH, Dept Quim Organ, Zaragoza 50009, Spain

来源：

AMINO ACIDS | 2021年 / 53卷 / 03期

关键词：

Wittig-Horner and Pictet-Spengler reactions; alpha; beta-Dehydroaminophosphonate; N-Acyliminium ion; Radical fragmentation; Phosphorylation; alpha-Aminophosphonic acids; 1ST;

D O I：

10.1007/s00726-021-02962-4

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Two new strategies for the efficient synthesis of racemic 1,2,3,4-tetrahydroisoquinoline-3-phosphonic acid (Tic(p)) (+/-)-2 have been developed. The first strategy involves the electron-transfer reduction of the easily obtained alpha,beta-dehydro phosphonophenylalanine followed by a Pictet-Spengler cyclization. The second strategy involves a radical decarboxylation-phosphorylation reaction on 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic). In both strategies, the highly electrophilic N-acyliminium ion is formed as a key intermediate, and the target compound is obtained in good yield using mild reaction conditions and readily available starting materials, complementing existing methodologies and contributing to the easy accessibility of (+/-)-2 for further research.

引用

页码：451 / 459

页数：9

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