SYNTHESIS OF ARISTOTELIA-TYPE ALKALOIDS .5. BIOMIMETIC SYNTHESIS OF (+/-)-ARISTOMAKINE AND (+/-)-ARISTOMAKININE

被引：9

作者：

BURKARD, S ^{[1
]}

BORSCHBERG, HJ ^{[1
]}

机构：

[1] SWISS FED INST TECHNOL,ORGAN CHEM LAB,UNIV STR 16,CH-8092 ZURICH,SWITZERLAND

来源：

HELVETICA CHIMICA ACTA | 1990年 / 73卷 / 02期

关键词：

D O I：

10.1002/hlca.19900730209

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Biomimetic syntheses of racemic aristomakinine ((±)‐3) and aristomakine ((±)‐4), an unusual indole alkaloid bearing an N‐isopropyl group, are described. The key step is a Grob‐type fragmentation of anti‐15‐aristotelinyl methanesulfonate ((±)‐2) to the intermediate iminium ion I which, upon subsequent hydrolysis, furnished aristomakinine ((±)‐3). On the other hand, the same intermediate could be reduced in situ to aristomakine ((±)‐4). The controversial relative configurations of the two alkaloids have been firmly established by means of NOE difference experiments. Copyright © 1990 Verlag GmbH & Co. KGaA, Weinheim

引用

页码：298 / 302

页数：5

共 32 条

[1]

ABE N, 1968, TETRAHEDRON LETT, P1993

[2] ARISTOTELINE, A NOVEL INDOLE ALKALOID - X-RAY STRUCTURAL DETERMINATION [J].

ANDERSON, BF ;

ROBERTSON, GB ;

AVEY, HP ;

DONOVAN, WF ;

BICK, IRC ;

BREMNER, JB ;

FINNEY, AJT ;

PRESTON, NW ;

GALLAGHER, RT ;

RUSSELL, GB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (13) :511-512

[3] APPLICATIONS OF INTRAMOLECULAR NUCLEAR OVERHAUSER EFFECT IN STRUCTURAL ORGANIC CHEMISTRY [J].

BACHERS, GE ;

SCHAEFER, T .

CHEMICAL REVIEWS, 1971, 71 (06) :617-+

[4] CORRELATION OF INTRAMOLECULAR NUCLEAR OVERHAUSER EFFECT WITH INTERNUCLEAR DISTANCE [J].

BELL, RA ;

SAUNDERS, JK .

CANADIAN JOURNAL OF CHEMISTRY, 1970, 48 (07) :1114-&

[5]

BELL RA, 1968, J CHEM SOC CHEM COMM, P1093

[6]

BICK IRC, 1981, TETRAHEDRON LETT, P3275

[7]

BICK IRC, 1981, HETEROCYCLES, V16, P1301

[8]

BICK IRC, 1980, TETRAHEDRON LETT, P545

[9]

BICK IRC, 1985, ALKALOIDS, V24, pCH3

[10] CONSTRUCTION OF LARGE CARBOCYCLIC RINGS BY IRELAND-CLAISEN REARRANGEMENT OF O-SILYLATED LACTONE ENOLATES - SYNTHESIS OF (+/-)-MUSCONE [J].

BRUNNER, RK ;

BORSCHBERG, HJ .

HELVETICA CHIMICA ACTA, 1983, 66 (08) :2608-2614

← 1 2 3 4 →