Efficient Total Synthesis of (+)-Dihydropinidine, (-)-Epidihydropinidine, and (-)-Pinidinone

被引：37

作者：

Kavala, Miroslav ^{[1
]}

Mathia, Frantisek ^{[1
]}

Kozisek, Jozef ^{[2
]}

Szolcsanyi, Peter ^{[1
]}

机构：

[1] Slovak Univ Technol Bratislava, Dept Organ Chem, SK-81237 Bratislava, Slovakia

[2] Slovak Univ Technol Bratislava, Dept Phys Chem, SK-81237 Bratislava, Slovakia

来源：

JOURNAL OF NATURAL PRODUCTS | 2011年 / 74卷 / 04期

关键词：

PALLADIUM-CATALYZED OXIDATION; PIPERIDINE ALKALOIDS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; MOLECULAR-OXYGEN; OLEFINS; ROUTE; (-)-DIHYDROPINIDINE; REDUCTION;

D O I：

10.1021/np100852p

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

The 2,6-disubstituted piperidine alkaloids (+)-dihydropinidine (1), (-)-epidihydropinidine (2) (as HCl salts), and (-) pinidinone (3) were efficiently synthesized from (S)-epichlorohidrin. (7) as common substrate using regioselective Wacker-Tsuji oxidation of alkenylazides 10 and 14 as well as a highly diastereoselective reduction of cyclic imine 11 as key steps. The protecting group free total syntheses represent the up to date shortest routes with highest overall yields for all three naturally occurring alkaloids (1 3). The first single crystal X-ray analysis of (-)-epidihydropinidine hydrochloride (2.HCl) confirmed its proposed absolute configuration to; be (2S,6S) corresponding to that of the isolated natural product

引用

页码：803 / 808

页数：6

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