CONVERSION OF AVERMECTIN-B1 TO 19-EPI-AVERMECTIN-B1

被引：10

作者：

BLIZZARD, T

BOSTROM, L

MARGIATTO, G

MROZIK, H

FISHER, M

机构：

[1] Merck Sharp Dohme Research Laboratories R50G-231, Rahway, NJ 07065

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 24期

关键词：

D O I：

10.1016/0040-4039(91)85068-G

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Avermectin B1 (1) has been converted to 19-epi-avermectin B1 (2) in six steps. Analog 2 retains some bioactivity but is substantially less bioactive than 1.

引用

页码：2723 / 2726

页数：4

共 19 条

[11] AVERMECTIN CHEMISTRY - PROBLEMS OF CONJUGATION, DECONJUGATION, AND EPIMERIZATION [J].

FRASERREID, B ;

WOLLEB, H ;

FAGHIH, R ;

BARCHI, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) :933-935

[12] STUDIES ON THE DECONJUGATION EPIMERIZATION STRATEGY EN-ROUTE TO AVERMECTIN-B1A - PROBLEMS AND SOLUTIONS [J].

HANESSIAN, S ;

DUBE, D ;

HODGES, PJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (23) :7063-7067

[13]

HANESSIAN S, 1986, J AM CHEM SOC, P108

[14] THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].

MITSUNOBU, O .

SYNTHESIS-STUTTGART, 1981, (01) :1-28

[15] FACILE SYNTHESIS OF LACTONES [J].

MUKAIYAMA, T ;

USUI, M ;

SAIGO, K .

CHEMISTRY LETTERS, 1976, (01) :49-50

[16] SOLUTION CONFORMATION OF THE DISACCHARIDE OF AVERMECTIN-B1A EXAMINED BY NMR-SPECTROSCOPY AND NUCLEAR OVERHAUSER ENHANCEMENT RESTRAINED HARD-SPHERE EXO-ANOMERIC EFFECT CALCULATION [J].

NESZMELYI, A ;

MACHYTKA, D ;

KMETY, A ;

SANDOR, P ;

LUKACS, G .

JOURNAL OF ANTIBIOTICS, 1989, 42 (10) :1494-1501

[17] BASE-CATALYZED ISOMERIZATION OF AVERMECTINS [J].

PIVNICHNY, JV ;

ARISON, BH ;

PREISER, FA ;

SHIM, JSK ;

MROZIK, H .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1988, 36 (04) :826-828

[18]

TIDWELL TT, 1990, SYNTHESIS-STUTTGART, P857

[19] SYNTHESIS OF AVERMECTIN-B1A AGLYCON [J].

WHITE, JD ;

BOLTON, GL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (04) :1626-1628

← 1 2 →