Versatile approach to enantiopure 2,6-disubstituted piperidin-3-ol framework: Application to the total synthesis of (+)-deoxoprosopinine

被引：35

作者：

Wang, Q ^{[1
]}

Sasaki, NA ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 14期

关键词：

D O I：

10.1021/jo0496291

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of enantiopure 2,6-disubstituted piperidin-3-ol 19 is developed featuring two key steps: (a) Julia olefination of (2R)-3-phenylsulfonyl-2-tert-butyloxycarbamoylpropanol benzyl ether 9B and (2R,3S)-2-tert-butyldiphenyl-3,4-O-isopropylidine-2,3,4-trihydroxybutyraldehyde 8 and (b) intramolecular N-alkylation. A straightforward asymmetric synthesis of (+)-deoxoprosopinine (2) from 19 is described demonstrating the versatility of this novel approach.

引用

页码：4767 / 4773

页数：7

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