NEW BIOGENETIC-TYPE APPROACH TO CEPHALOTAXUS ALKALOIDS AND MECHANISM OF SCHELHAMMERA-TYPE HOMOERYTHRINADIENONE FORMATION INVITRO

被引：12

作者：

KUPCHAN, SM ^{[1
]}

DHINGRA, OP ^{[1
]}

KIM, CK ^{[1
]}

机构：

[1] UNIV VIRGINIA,DEPT CHEM,CHARLOTTESVILLE,VA 22901

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1978年 / 43卷 / 23期

关键词：

D O I：

10.1021/jo00417a015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three monophenolic dibenz[d, f]azecines, 3b, 3c, and 3d, were synthesized by taking advantage of VOF3-TFA/ TFAA induced oxidative coupling of nonphenolic and monophenolic phenethyltetrahydroisoquinolines to homoneospirinedienones and homoproerythrinadienones. The oxidation of 2-hydroxydibenz[d, f]azecine 3b with potassium ferricyanide yielded the cephalotaxine precursor 5b (10%), which represents the first reported synthesis of such a compound along the biogenetic-type route. Similar oxidation of 3-hydroxydibenz[d, f]azecine 3c gave naturally unknown homoerysodienone 6b in 15% yield. However, when 12-hydroxydibenz[d, f]azecine 3d was oxidized, no Schelhammera-type homoerythrinadienone 7b was detectable. This implies that the diphenoquinone 4 may be an intermediate in the formation of the Schelhammera-type homoerythrinadienone. © 1978, American Chemical Society. All rights reserved.

引用

页码：4464 / 4468

页数：5

共 19 条

[1] ALKALOIDS ISOLATED FROM CEPHALOTAXUS-DURPACEA SIEB ET ZUCC [J].