An Efficient Synthesis of Phenanthroindolizidine Core via Hetero Diels-Alder Reaction of In Situ Generated α-Allenylchalcogenoketenes With Cyclic Imines

被引：0

作者：

Shimada, Kazuaki ^{[1
]}

Suzuki, Mariko ^{[1
]}

Yahaba, Kohei ^{[1
]}

Aoyagi, Shigenobu ^{[1
]}

Takikawa, Yuji ^{[1
]}

Korenaga, Toshinobu ^{[1
]}

机构：

[1] Iwate Univ, Fac Sci & Engn, Dept Chem, Morioka, Iwate 0208551, Japan

来源：

NATURAL PRODUCT COMMUNICATIONS | 2019年 / 14卷 / 06期

关键词：

alkynyl propargyl sufide; alkynyl propargyl selenide; alpha-allenylthioketene; alpha-allenylselenoketene; hetero Diels-Alder reaction; indolizidine; phenanthroindolizidine; PHENANTHROQUINOLIZIDINE ALKALOIDS; INDOLIZIDINE; QUINOLIZIDINE; CYCLIZATION; ALLENYLTRIMETHYLSILYLTHIOKETENES; PHOTOCYCLIZATION; CYCLOADDITION; PHENANTHRENE; CHEMISTRY; REAGENTS;

D O I：

10.1177/1934578X19857489

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Synthesis of phenanthroindolizidine core was efficiently achieved through a pathway involving hetero Diels-Alder reaction of alpha-allenylchalcogenoketenes, generated in situ by thermal [3,3] sigmatropic rearrangement of alkynyl propargyl sulfides or selenides, with cyclic imines and the subsequent iodine-assisted photochemical cyclization.

引用

页数：13

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