First total synthesis of A2 isoprostane

被引：44

作者：

Zanoni, G ^{[1
]}

Porta, A ^{[1
]}

Vidari, G ^{[1
]}

机构：

[1] Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 12期

关键词：

D O I：

10.1021/jo025652f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective Julia-Lythgoe olefination has allowed the first total synthesis of A(2) isoprostane (1), a recently discovered member of the growing isoprostane family. This elusive compound opens up numerous new avenues for the molecular biology of cyclopentenone prostaglandins, which are endowed of intriguing biological effects such as antitumor, antiinflammatory, and antiviral activities.

引用

页码：4346 / 4351

页数：6

共 24 条

[1]

ACMATOVICH B, 1988, TETRAHEDRON, V44, P4989

[2] REGIO-SELECTIVITY AND STEREO-SELECTIVITY OF ALKENYL RADICAL RING-CLOSURE - A THEORETICAL-STUDY [J].

BECKWITH, ALJ ;

SCHIESSER, CH .

TETRAHEDRON, 1985, 41 (19) :3925-3941

[3] REGIO-SELECTIVITY AND STEREO-SELECTIVITY IN RADICAL REACTIONS [J].

BECKWITH, ALJ .

TETRAHEDRON, 1981, 37 (18) :3073-3100

[4] TOTAL SYNTHESIS OF PROSTAGLANDIN-A2 INVOLVING THE REACTION OF A HETEROCUPRATE REAGENT WITH AN ALLYL EPOXIDE [J].

CHAPLEO, CB ;

FINCH, MAW ;

LEE, TV ;

ROBERTS, SM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (10) :2084-2087

[5] Formation of reactive cyclopentenone compounds in vivo as products of the isoprostane pathway [J].

Chen, Y ;

Morrow, JD ;

Roberts, LJ .

JOURNAL OF BIOLOGICAL CHEMISTRY, 1999, 274 (16) :10863-10868

[6] Evidence for the formation of a novel cyclopentenone isoprostane, 15-A2t-isoprostane (8-iso-prostaglandin A2) in vivo [J].

Chen, Y ;

Zackert, WE ;

Roberts, LJ ;

Morrow, JD .

BIOCHIMICA ET BIOPHYSICA ACTA-MOLECULAR AND CELL BIOLOGY OF LIPIDS, 1999, 1436 (03) :550-556

[7]

Corey E. J., 1989, LOGIC CHEM SYNTHESIS, P17

[8]

Curran D. P., 1996, STEREOCHEMISTRY RADI

[9] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[10] ELIMINATION AND ADDITION-REACTIONS .43. ELIMINATIVE FISSION OF CYCLOBUTANES AND THE RELATIONSHIP BETWEEN STRAIN AND REACTIVITY IN CYCLOBUTANES AND CYCLOPROPANES [J].

EARL, HA ;

STIRLING, CJM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (09) :1273-1280

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