Chemoenzymatic and electrochemical oxidations in the synthesis of octahydroisoquinolines for conversion to morphine. Relative merits of radical vs. acid-catalyzed cyclizations.

被引：18

作者：

Endoma, MA ^{[1
]}

Butora, G ^{[1
]}

Claeboe, CD ^{[1
]}

Hudlicky, T ^{[1
]}

Abboud, KA ^{[1
]}

机构：

[1] UNIV FLORIDA,DEPT CHEM,GAINESVILLE,FL 32611

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 51期

关键词：

D O I：

10.1016/S0040-4039(97)10384-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Second-generation stereoselective synthesis of octahydroisoquinoline 3, a potential key intermediate for the projected synthesis of the natural enantiomer of morphine, has been accomplished in five steps from arene cis-diol 8. Electrochemical oxidation of 9b furnished 7b, a precursor for the key benzoate-assisted acyl-iminium cyclization. (C) 1997 Elsevier Science Ltd.

引用

页码：8833 / 8836

页数：4

共 21 条

[1]

[Anonymous], STUDIES NATURAL PROD

[2]

[Anonymous], [No title captured]

[3] Electrochemical versus anionic oxygenation of azathymine derivatives [J].