Total synthesis of ent-sedridine using proline-catalyzed asymmetric addition as a key step

被引：17

作者：

Itoh, Takashi ^{[1
]}

Nishimura, Kosuke ^{[1
]}

Nagata, Kazuhiro ^{[1
]}

Yokoya, Masashi ^{[1
]}

机构：

[1] Showa Univ, Sch Pharmceut Sci, Shinagawa Ku, Tokyo 1428555, Japan

来源：

SYNLETT | 2006年 / 14期

关键词：

asymmetric catalysis; nucleophilic additions; total synthesis; alkaloids; piperidine;

D O I：

10.1055/s-2006-948203

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of ent-sedridine is described. The development of a new method for the construction of the C-2 chiral center of the piperidine ring was achieved using a proline-catalyzed Mannich reaction. Reaction of 4-hydroxybutanal and p-anisidine to form an imine and subsequent addition of acetone gave the key chiral aliphatic precursor with high enantioselectivity.

引用

页码：2207 / 2210

页数：4

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