Lipase-catalyzed enantioselective ring opening of unactivated alicyclic-fused β-lactams in an organic solvent

被引：85

作者：

Forró, E ^{[1
]}

Fulöp, F ^{[1
]}

机构：

[1] Univ Szeged, Inst Pharmaceut Chem, H-6701 Szeged, Hungary

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 08期

关键词：

D O I：

10.1021/ol034096o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient and very simple method was developed for the synthesis of enantiopure beta-amino acids (e.g. cispentacin) and beta-lactams through the enzyme-catalyzed enantioselective ring opening of unactivated alicyclic, beta-lactams in organic media. High enantioselectivity (E > 200) was observed when the Lipolase flipase B from Candida antarctica)-catalyzed reactions were performed with H2O (1 equiv) in dilsopropyl ether at 60 degreesC. The resolved products, obtained in good chemical yield (36-47%), could be easily separated.

引用

页码：1209 / 1212

页数：4

共 52 条

[41] Synthesis of (±)-anatoxin-a and analogues [J].

Parsons, PJ ;

Camp, NP ;

Edwards, N ;

Sumoreeah, LR .

TETRAHEDRON, 2000, 56 (02) :309-315

[42] Tandem reactions of anions: A short and efficient route to +/-anatoxin-A [J].

Parsons, PJ ;

Camp, NP ;

Underwood, JM ;

Harvey, DM .

TETRAHEDRON, 1996, 52 (35) :11637-11642

[43] Synthesis and 12-helical secondary structure of β-peptides containing (2R,3R)-aminoproline [J].

Porter, EA ;

Wang, XF ;

Schmitt, MA ;

Gellman, SH .

ORGANIC LETTERS, 2002, 4 (19) :3317-3319

[44] Antibiotics -: Non-haemolytic β-amino-acid oligomers [J].

Porter, EA ;

Wang, XF ;

Lee, HS ;

Weisblum, B ;

Gellman, SH .

NATURE, 2000, 404 (6778) :565-565

[45] beta-peptides: a surprise at every turn [J].

Seebach, D ;

Matthews, JL .

CHEMICAL COMMUNICATIONS, 1997, (21) :2015-2022

[46] SYNTHESIS AND BIOLOGICAL EVALUATION OF 6-AZABICYCLO[3.2.0]HEPT-2-ENE DERIVATIVES AS POTENTIAL ANTIBACTERIAL AGENTS AND BETA-LACTAMASE INHIBITORS [J].

SINGH, R ;

COOPER, RDG .

TETRAHEDRON, 1994, 50 (42) :12049-12064

[47] Enzymatic synthesis of monocyclic β-lactams [J].

Sleeman, MC ;

MacKinnon, CH ;

Hewitson, KS ;

Schofield, CJ .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (04) :597-599

[48] β-amino acids:: Versatile peptidomimetics [J].

Steer, DL ;

Lew, RA ;

Perlmutter, P ;

Smith, AI ;

Aguilar, MI .

CURRENT MEDICINAL CHEMISTRY, 2002, 9 (08) :811-822

[49] Synthesis and transformations of enantiomeric 1,2-disubstituted monoterpene derivatives [J].

Szakonyi, Z ;

Martinek, T ;

Hetényi, A ;

Fülöp, F .

TETRAHEDRON-ASYMMETRY, 2000, 11 (22) :4571-4579

[50] β-lactams as building blocks in the synthesis of macrocyclic spermine and spermidine alkaloids [J].

Wasserman, HH ;

Matsuyama, H ;

Robinson, RP .

TETRAHEDRON, 2002, 58 (35) :7177-7190

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