ALLYLTIN REAGENTS - A GENERAL-APPROACH TO CARBON-CARBON BOND FORMATION APPLIED TO PENICILLIN DERIVED AZETIDINONES .1.

被引：16

作者：

BLASZCZAK, LC

ARMOUR, HK

HALLIGAN, NG

机构：

[1] Lilly Research Laboratories, Eli Lilly and Company, Indianapolis

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 40期

关键词：

D O I：

10.1016/S0040-4039(00)97934-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allyltributyltin has been shown to be a useful reagent for allyl transfer to penicillin derived azetidinones. The radical mechanism of the reaction has been demonstrated and its stereochemical consequences recorded. The process opens new possibilities for the semi-synthesis of novel bicyclic β-lactam antibiotics from penicillin or cephalosporin. © 1990.

引用

收藏

页码：5693 / 5696

页数：4

相关论文

共 21 条

[1] AN ENANTIOSELECTIVE SYNTHESIS OF LORACARBEF (LY163892/KT3777) [J].

BODUROW, CC ;

BOYER, BD ;

BRENNAN, J ;

BUNNELL, CA ;

BURKS, JE ;

CARR, MA ;

DOECKE, CW ;

ECKRICH, TM ;

FISHER, JW ;

GARDNER, JP ;

GRAVES, BJ ;

HINES, P ;

HOYING, RC ;

JACKSON, BG ;

KINNICK, MD ;

KOCHERT, CD ;

LEWIS, JS ;

LUKE, WD ;

MOORE, LL ;

MORIN, JM ;

NIST, RL ;

PRATHER, DE ;

SPARKS, DL ;

VLADUCHICK, WC .

TETRAHEDRON LETTERS, 1989, 30 (18) :2321-2324

[2] PYRROLIZIDINONE AND INDOLIZIDINONE SYNTHESIS - GENERATION AND INTRAMOLECULAR ADDITION OF ALPHA-ACYLAMINO RADICALS TO OLEFINS AND ALLENES [J].

BURNETT, DA ;

CHOI, JK ;

HART, DJ ;

TSAI, YM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (26) :8201-8209

[3]

COUNTER FT, 1987, 27TH AM SOC MICR INT

[4] THE ASYMMETRIC-SYNTHESIS OF BETA-LACTAM ANTIBIOTICS .2. THE 1ST ENANTIOSELECTIVE SYNTHESIS OF THE CARBACEPHALOSPORIN NUCLEUS [J].

EVANS, DA ;

SJOGREN, EB .

TETRAHEDRON LETTERS, 1985, 26 (32) :3787-3790

[5] PRACTICAL PREPARATION OF 4(R)-ALLYLAZETIDINONES AND 4(R)-(1-METHYLALLYL)AZETIDINONES [J].

FLIRI, H ;

MAK, CP .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (19) :3438-3442

[6] FROM PENICILLIN TO PENEM AND CARBAPENEM .6. SYNTHESIS OF DETHIATHIENAMYCIN [J].

FUJIMOTO, K ;

IWANO, Y ;

HIRAI, K .

TETRAHEDRON LETTERS, 1985, 26 (01) :89-92

[7]

Giese B., 1986, ORG CHEM SERIES, P98

[8]

GRIGNON J, 1973, J ORGANOMET CHEM, V33, P61

[9] TOTAL SYNTHESIS OF BETA-LACTAM ANTIBIOTICS .8. STEREOSPECIFIC TOTAL SYNTHESIS OF (+/-)-1-CARBACEPHALOTHIN [J].

GUTHIKONDA, RN ;

CAMA, LD ;

CHRISTENSEN, BG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (24) :7584-7585

[10]

HALLIGAN NG, 1989, ORG SYNTH, V68, P104