CHIROSPECIFIC SYNTHESES OF NITROGEN AND SIDE-CHAIN MODIFIED ANATOXIN ANALOGS - SYNTHESIS OF (1R)-ANATOXINAL AND (1R)-ANATOXINIC ACID-DERIVATIVES

被引：43

作者：

HOWARD, MH ^{[1
]}

SARDINA, FJ ^{[1
]}

RAPOPORT, H ^{[1
]}

机构：

[1] UNIV CALIF BERKELEY,DEPT CHEM,BERKELEY,CA 94720

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 09期

关键词：

D O I：

10.1021/jo00296a050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward and good yielding route to side-chain analogues of the potent neurotoxin and neurotransmitter (+)-anatoxin (1) has been developed. Peroxy acid oxidation of the (silyloxy)butadiene 43 derived from readily synthesized, optically pure (Ifl)-t-BOC-anatoxin (42) affords silyloxy ketone 44. Fluorolysis of 44 followed by oxidative cleavage of the resultant α-hydroxy ketone 45 gives a mixture of αβ-unsaturated acid 46 and ester 41 in 57% combined yield. Other approaches to these compounds, based on literature precedent, failed. (lfl)-i-BOC-anatoxinic acid (46) then serves as educt for the synthesis of a wide variety of anatoxin derivatives with modified side-chain functionality. These analogues, designed to serve as probes of the agonist binding site of the nicotinic acetylcholine receptor, include alcohol, aldehyde, amide, hydroxamate, and oxime ether functional groups. © 1990, American Chemical Society. All rights reserved.

引用

页码：2829 / 2838

页数：10

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