Synthesis of axinohydantoins

被引：51

作者：

Carolina, A ^{[1
]}

Sosa, B ^{[1
]}

Yakushijin, K ^{[1
]}

Horne, DA ^{[1
]}

机构：

[1] Oregon State Univ, Dept Chem, Corvallis, OR 97331 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 13期

关键词：

D O I：

10.1021/jo020063v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short synthesis of the hydantoin-containing marine sponge metabolites axinohydantoins is described. A key feature of the synthesis is a putative biomimetic, intramolecular cyclization of alpha-functionalized imidazolone 5, which affords the tricyclic pyrroloazepinone framework comprising 6. In addition, the conversion of imidazolones to alpha,beta-unsaturated hydantoins is outlined and represents a new approach to these heterocyclic systems.

引用

页码：4498 / 4500

页数：3

共 17 条

[1] The synthesis of imidazole derivatves from alpha-amino acids, I Announcement - A new synthesis of desamino-histidine and an article concerning information on ergothionein [J].

Akabori, S .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1933, 66 :151-158

[2] PYRROLE ANTIBACTERIAL AGENTS .2. 4,5-DIHALOPYRROLE-2-CARBOXYLIC ACID DERIVATIVES [J].

BAILEY, DM ;

JOHNSON, RE .

JOURNAL OF MEDICINAL CHEMISTRY, 1973, 16 (11) :1300-1302

[3] ISOLATION AND X-RAY CRYSTAL-STRUCTURE OF A NOVEL BROMO-COMPOUND FROM 2 MARINE SPONGES [J].

CIMINO, G ;

DEROSA, S ;

DESTEFANO, S ;

MAZZARELLA, L ;

PULITI, R ;

SODANO, G .

TETRAHEDRON LETTERS, 1982, 23 (07) :767-768

[4] New alkaloids from the Indopacific sponge Stylissa carteri [J].

Eder, C ;

Proksch, P ;

Wray, V ;

Steube, K ;

Bringmann, G ;

van Soest, RWM ;

Sudarsono ;

Ferdinandus, E ;

Pattisina, LA ;

Wiryowidagdo, S ;

Moka, W .

JOURNAL OF NATURAL PRODUCTS, 1999, 62 (01) :184-187

[5] Marine natural products [J].

Faulkner, DJ .

NATURAL PRODUCT REPORTS, 2001, 18 (01) :1-49

[6] Spongiacidins A-D, new bromopyrrole alkaloids from Hymeniacidon sponge [J].

Inaba, K ;

Sato, H ;

Tsuda, M ;

Kobayashi, J .

JOURNAL OF NATURAL PRODUCTS, 1998, 61 (05) :693-695

[7]

KITAGAWA I, 1983, CHEM PHARM BULL, V31, P2321

[8] HYMENIN, A NOVEL ALPHA-ADRENOCEPTOR BLOCKING-AGENT FROM THE OKINAWAN MARINE SPONGE HYMENIACIDON SP [J].

KOBAYASHI, J ;

OHIZUMI, Y ;

NAKAMURA, H ;

HIRATA, Y ;

WAKAMATSU, K ;

MIYAZAWA, T .

EXPERIENTIA, 1986, 42 (09) :1064-1065

[9] 2-MERCAPTOGLYOXALINES .9. THE PREPARATION OF 1-5-DISUBSTITUTED 2-MERCAPTOGLYOXALINES FROM ALPHA-AMINO-ACIDS [J].

LAWSON, A ;

MORLEY, HV .

JOURNAL OF THE CHEMICAL SOCIETY, 1955, :1695-1698

[10] Z-axinohydantoin and debromo-z-axinohydantoin from the sponge Stylotella aurantium: Inhibitors of protein kinase C [J].

Patil, AD ;

Freyer, AJ ;

Killmer, L ;

Hofmann, G ;

Randall, K .

NATURAL PRODUCT LETTERS, 1997, 9 (03) :201-207

← 1 2 →