Synthesis of four-membered ring spiro-β-lactams by epoxide ring-opening

被引：13

作者：

Benfatti, Fides ^{[1
]}

Cardillo, Giuliana ^{[1
]}

Gentilucci, Luca ^{[1
]}

Tolomelli, Alessandra ^{[1
]}

机构：

[1] Univ Bologna, Dipartmento Chim, I-40126 Bologna, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 19期

关键词：

lactams; oxygen heterocycles; spiro compounds; ring-opening; regio selectivity; HUMAN CYTOMEGALOVIRUS PROTEASE; 3,4-DISUBSTITUTED AZETIDINONES; STEREOSELECTIVE-SYNTHESIS; SELECTIVE INHIBITORS; ASYMMETRIC-SYNTHESIS; SERINE-PROTEASE; LEWIS-ACIDS; CATHEPSIN-K; TRANSPOSITION; MONOBACTAMS;

D O I：

10.1002/ejoc.200601110

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of hydroxy epoxides have been obtained from well defined hydroxy-alkenyl derivatives. Their subsequent intramolecular ring-opening allowed unprecedented classes of spiro-lactams to be obtained. The effect of the epoxide stereochemistry and of the reaction temperature on the regioselective formation of five- or four-membered ring spiro derivatives was explored. This transformation is part of a program directed towards the synthesis of polyfunctionalized beta-lactams as cholesterol absorption inhibitors (CAIs).

引用

页码：3199 / 3205

页数：7

共 54 条

[41] HARD AND SOFT ACIDS AND BASES [J].

PEARSON, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (22) :3533-&

[42] Solution-phase synthesis of a combinatorial monocyclic β-lactam library:: Potential protease inhibitors [J].

Pitlik, J ;

Townsend, CA .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (24) :3129-3134

[43]

Roveri O.A., 1995, CURR MED CHEM, V1, P441

[44] 3,4-disubstituted azetidinones as selective inhibitors of the cysteine protease cathepsin K. Exploring P3 elements for potency and selectivity [J].

Setti, EL ;

Davis, D ;

Janc, JW ;

Jeffery, DA ;

Cheung, H ;

Yu, W .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (05) :1529-1534

[45] 3,4-disubstituted azetidinones as selective inhibitors of the cysteine protease cathepsin K. Exploring P2 elements for selectivity [J].

Setti, EL ;

Davis, D ;

Chung, T ;

McCarter, J .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (12) :2051-2053

[46]

SHIMIZU M, 1992, SYNLETT, P204

[47] β-lactams in the new millennium.: Part-I:: Monobactams and carbapenems [J].

Singh, GS .

MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2004, 4 (01) :69-92

[48]

SMITH JG, 1984, SYNTHESIS-STUTTGART, P629

[49] β-oxidation of α,β-unsaturated carbonyl compounds [J].

Sommer, TJ .

SYNTHESIS-STUTTGART, 2004, (02) :161-201

[50]

Southgate R., 1993, Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, P621, DOI DOI 10.1002/ADSC.201400191

← 1 2 3 4 5 6 →