Biomimetic Approach toward the Total Synthesis of rac-2-(Acylmethylene)pyrrolidine Alkaloids

被引：11

作者：

Shih, Yu-Chiao ^{[1
]}

Tsai, Pei-Hua ^{[1
]}

Hsu, Chia-Chun ^{[1
]}

Chang, Chih-Wei ^{[1
]}

Jhong, Yuandong ^{[1
]}

Chen, Yun-Chung ^{[1
]}

Chien, Tun-Cheng ^{[1
]}

机构：

[1] Natl Taiwan Normal Univ, Dept Chem, Taipei 11677, Taiwan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 13期

关键词：

ALPHA-AMINO-ACIDS; PYRROLIDINE ALKALOIDS; PHENANTHROINDOLIZIDINE ALKALOIDS; ENANTIOSPECIFIC SYNTHESIS; CHIROSPECIFIC SYNTHESIS; CARBON NUCLEOPHILES; BENZOYLACETIC ACID; TROPANE ALKALOIDS; DERIVATIVES; ANALOGS;

D O I：

10.1021/acs.joc.5b00836

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-(Acylmethylne)pyrrolidine derivatives were synthesized via intermolecular decarbonylative Mannich reaction from various methyl ketones and 1-alkyl-1-pyrroliniums, generated in situ from 1-alkylprolines. This approach mimics the biosynthetic pathway and provides a direct access to a series of 2-(acylmethylene)-pyrrolidine alkaloids, including hygrine, N-methylruspolinone, dehydrodarlinine, and ruspolinone.

引用

页码：6669 / 6678

页数：10

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