Expedient Pyrrolizidine Synthesis by Propargylsilane Addition to N-Acyliminium Ions followed by Gold-Catalyzed α-Allenyl Amide Cyclization

被引：37

作者：

Breman, Arjen C. ^{[1
]}

Dijkink, Jan ^{[1
]}

van Maarseveen, Jan H. ^{[1
]}

Kinderman, Sape S. ^{[1
]}

Hiemstra, Henk ^{[1
]}

机构：

[1] Univ Amsterdam, Vant Hoff Inst Mol Sci, NL-1018 WS Amsterdam, Netherlands

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 16期

关键词：

INTRAMOLECULAR HYDROAMINATION; STEREOSELECTIVE-SYNTHESIS; ALKALOID SYNTHESIS; AMINO-ACID; (+)-HELIOTRIDINE; CYCLOISOMERIZATION; INDOLIZIDINE; AMINOALLENES; METATHESIS; CHEMISTRY;

D O I：

10.1021/jo901393y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A reaction sequence, involving the addition of (substituted) propargylsilanes to lactate-derived N-acyliminium ions followed by gold-catalyzed cyclization of the resulting alpha-allenyl amide, is applied in expedient syntheses of pyrrolizidine alkaloids heliotridine and ent-retronecine in five steps from (S)-malic acid.

引用

页码：6327 / 6330

页数：4

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