Synthesis of the cyclic prenylguanidine nitensidine E using a palladium-catalyzed carbenylative amination

被引：14

作者：

Kitamura, Mitsuru ^{[1
]}

Yuasa, Ryohei ^{[1
]}

Van Vranken, David L. ^{[2
]}

机构：

[1] Kyushu Inst Technol, Dept Appl Chem, Tobata Ku, Kitakyushu, Fukuoka 8048550, Japan

[2] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 23期

关键词：

Palladium; Carbenylation; Guanidine; Alkaloid; TRANSITION-METAL CATALYSIS; EFFICIENT TOTAL-SYNTHESIS; CROSS-COUPLING REACTIONS; CARBON BOND FORMATION; N-TOSYLHYDRAZONES; CONTROLLED CARBOMETALATION; GUANIDINE ALKALOIDS; CARBENE INSERTION; DIAZO-COMPOUNDS; VINYL HALIDES;

D O I：

10.1016/j.tetlet.2014.10.140

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We demonstrate the utility of carbenylative aminations in the synthesis of the cyclic alkaloid nitensidine E involving both protected and un-protected guanidine moieties. The alkylguanidine substrate is generated using a Mitsunobu reaction and we show that NH chemical shifts correlate with the regiochemistry and tautomeric structure of N-alkyl-bis-N,N'-Boc-guanidines. When the doubly-protected guanidine is used as a substrate in the palladium reaction, the catalyst assembles the heterocyclic ring and quaternary center of nitensidine E but with concomitant loss of one of the Boc groups. The reaction also works with an un-protected guanidine leading directly to nitensidine E. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：3027 / 3031

页数：5

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