A general and stereoselective synthesis of the capsaicinoids via the orthoester Claisen rearrangement

被引：29

作者：

Kaga, H ^{[1
]}

Goto, K ^{[1
]}

Takahashi, T ^{[1
]}

Hino, M ^{[1
]}

Tokuhashi, T ^{[1
]}

Orito, K ^{[1
]}

机构：

[1] HOKKAIDO UNIV,GRAD SCH ENGN,DIV MOL CHEM,ORGAN SYNTH LAB,SAPPORO,HOKKAIDO 060,JAPAN

来源：

TETRAHEDRON | 1996年 / 52卷 / 25期

关键词：

D O I：

10.1016/0040-4020(96)00414-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Capsaicin, a main pungent principle of hot pepper, and its 15 analogs have been efficiently synthesized. The key step of this synthetic sheme is the orthoester Claisen rearrangement, which transformed allylic alcohols 2A-C to (E)-alkenoates 3A-C (E/Z > 100) in a highly stereoselective manner. The subsequent carbon chain elongations on 3 based on the cyanation or the malonic acid ester synthesis afforded (E)-alkenoic acids 8, which were converted to the corresponding acid chloride and then coupled with vanillylamine to give capsaicinoids. HPLC and CE (capillary electrophoresis) analyses of these capsaicinoids were also carried out. (C) 1996 Elsevier Science Ltd

引用

页码：8451 / 8470

页数：20

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