SYNTHESIS OF AVERMECTIN-B1-4'',4''A-OXIDE - A PRECURSOR OF POTENT ANTHELMINTIC AGENTS

被引：7

作者：

MEINKE, PT

SINCLAIR, P

MROZIK, H

OCONNOR, S

OSTLIND, DA

SHOOP, WL

ARISON, BH

FISHER, MH

机构：

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1992年 / 2卷 / 06期

关键词：

D O I：

10.1016/S0960-894X(01)81193-8

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Treatment of 4"-oxo-5-OTBDMS-Avermectin B1 (2) with trimethylsilyldiazomethane or diazomethane resulted in the stereoselective formation of the 4",4"a-oxide (3) in addition to the ring-expanded oxepinyl epoxide (4). The resultant epoxides were opened regiospecifically with sulfur, amine and halogen nucleophiles. The new 4"-substituted avermectins thus formed exhibited potent, broad-spectrum anthelmintic activity.

引用

收藏

页码：537 / 540

页数：4

相关论文

共 23 条

[1] SUBSTITUENT EFFECTS ON THE REGIOSELECTIVITY OF ONE-CARBON RING EXPANSIONS OF 7-OXABICYCLO[2.2.1]HEPTAN-2-ONE DERIVATIVES WITH DIAZOMETHANE [J].

AUBERSON, Y ;

BIMWALA, RM ;

VOGEL, P .

TETRAHEDRON LETTERS, 1991, 32 (13) :1637-1640

[2]

BASHA A, 1977, TETRAHEDRON LETT, V48, P4171

[3]

BLIZZARD T, 1990, RECENT PROGRESS IN THE CHEMICAL SYNTHESIS OF ANTIBIOTICS, P65

[4] BRINE SHRIMP (ARTEMIA-SALINA) AS A CONVENIENT BIOASSAY FOR AVERMECTIN ANALOGS [J].

BLIZZARD, TA ;

RUBY, CL ;

MROZIK, H ;

PREISER, FA ;

FISHER, MH .

JOURNAL OF ANTIBIOTICS, 1989, 42 (08) :1304-1307

[5] IVERMECTIN, A NEW BROAD-SPECTRUM ANTI-PARASITIC AGENT [J].

CHABALA, JC ;

MROZIK, H ;

TOLMAN, RL ;

ESKOLA, P ;

LUSI, A ;

PETERSON, LH ;

WOODS, MF ;

FISHER, MH ;

CAMPBELL, WC ;

EGERTON, JR ;

OSTLIND, DA .

JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (10) :1134-1136

[6] THE TOTAL SYNTHESIS OF AVERMECTIN-A1A [J].

DANISHEFSKY, SJ ;

ARMISTEAD, DM ;

WINCOTT, FE ;

SELNICK, HG ;

HUNGATE, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (08) :2967-2980

[7] ALPHA-HALO KETONES .10. REGIOSPECIFIC HOMOLOGATION OF UNSYMMETRICAL KETONES [J].

DAVE, V ;

WARNHOFF, EW .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (15) :2590-2598

[8]

DAVIS HG, 1986, NAT PROD REP, P87

[9] DILITHIUM TETRABROMONICKELATE(II) AS A SOURCE OF SOFT NUCLEOPHILIC BROMIDE - REACTION WITH EPOXIDES [J].

DAWE, RD ;

MOLINSKI, TF ;

TURNER, JV .

TETRAHEDRON LETTERS, 1984, 25 (19) :2061-2064

[10]

Fisher M.H., 1984, MACROLIDE ANTIBIOTIC, P553