An expedient entry into the α-mercaptodiketopiperazine nucleus

被引：9

作者：

Hilton, ST

Motherwell, WB

Selwood, DL

机构：

[1] UCL, Dept Chem, Christopher Ingold Labs, London WC1H 0AJ, England

[2] UCL, Wolfson Inst Biomed Res, London WC1E 6BT, England

来源：

SYNLETT | 2004年 / 14期

关键词：

epidithiodiketopiperazine; multicomponent reactions; thiols; imines; sulfur;

D O I：

10.1055/s-2004-834823

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel approach to the alpha-mercaptodiketopiperazine nucleus is reported. which involved a three-component reaction of a number of amines with ethyl glyoxalate and para-methoxybenzylmercaptan. The subsequent products were readily elaborated to the monothiodiketopiperazine core structure.

引用

收藏

页码：2609 / 2611

页数：3

相关论文

共 30 条

[1] FURTHER EVIDENCE FOR THE INVOLVEMENT OF A MONOCYCLIC BETA-LACTAM IN THE ENZYMATIC CONVERSION OF DELTA-L-ALPHA-AMINOADIPOYL-L-CYSTEINYL-D-VALINE INTO ISOPENICILLIN-N [J].

BALDWIN, JE ;

BRADLEY, M ;

ADLINGTON, RM ;

NORRIS, WJ ;

TURNER, NJ .

TETRAHEDRON, 1991, 47 (03) :457-480

[2] REACTIONS OF UREAS WITH GLYOXYLIC-ACID AND METHYL GLYOXYLATE [J].

BENISHAI, D ;

ALTMAN, J ;

BERNSTEIN, Z .

TETRAHEDRON, 1977, 33 (10) :1191-1196

[3] DIFFERENTIALLY PROTECTED ALPHA-AMINOGLYCINE [J].

BOCK, MG ;

DIPARDO, RM ;

FREIDINGER, RM .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) :3718-3720

[4] Multi-purpose functionality for the structural elaboration of the piperazine-2,5-dione motif [J].

Chai, CLL ;

Elix, JA ;

Huleatt, PB .

TETRAHEDRON LETTERS, 2003, 44 (02) :263-265

[5] The first electrochemical study of epidithiopiperazine-2,5-diones, a special class of α,α′-disulfide bridged cyclic dipeptides [J].

Chai, CLL ;

Heath, GA ;

Huleatt, PB ;

O'Shea, GA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (03) :389-391

[6] Redox sensitive epidithiodioxopiperazines in biological mechanisms of toxicity [J].

Chai, CLL ;

Waring, P .

REDOX REPORT, 2000, 5 (05) :257-264

[7]

EICHNER RD, 1988, J BIOL CHEM, V263, P3772

[8] TOTAL SYNTHESIS OF GLIOTOXIN [J].

FUKUYAMA, T ;

KISHI, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (21) :6723-6724

[9] TOTAL SYNTHESIS OF GLIOTOXIN, DEHYDROGLIOTOXIN AND HYALODENDRIN [J].

FUKUYAMA, T ;

NAKATSUKA, S ;

KISHI, Y .

TETRAHEDRON, 1981, 37 (11) :2045-2078

[10] BIOSYNTHESIS OF GLIOTOXIN - SYNTHESIS OF SULFUR-BRIDGED DIOXOPIPERAZINES FROM N-HYDROXYAMINO ACIDS [J].

HERSCHEID, JDM ;

NIVARD, RJF ;

TIJHUIS, MW ;

OTTENHEIJM, HCJ .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (10) :1885-1888