Stereoselective synthesis of a cis-1,2-dialkylcyclopentane building block and its application in isoprostane synthesis (5-ent-F2c-IsoP)

被引：8

作者：

Elsner, Petteri ^{[1
]}

Jetter, Peter ^{[1
]}

Broedner, Kerstin ^{[1
]}

Helmchen, Guenter ^{[1
]}

机构：

[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 15期

关键词：

natural products; stereoselective synthesis; Wittig reaction; total synthesis; protecting groups;

D O I：

10.1002/ejoc.200800010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The all-cis substituted cyclopentane 3a, an analogue of the Corey lactone, has been prepared from a readily available nortricyclanone derivative by a five-step sequence in an overall yield of 34 %. This chiral building block has been applied in total syntheses of two diastereomeric isoprostanes belonging to the 5-F-2 family: ent-5-F-2c-IsoP (ent-1) and 5-epient-5-F(2)c-IsoP (ent-2). Key features of the syntheses are the introduction of the two unsaturated alkyl side chains through an E-selective Horner-Wadsworth-Emmons reaction with the base-sensitive syn-aldehyde 10, along with a Z-selective Wittig olefination. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

引用

页码：2551 / 2563

页数：13

共 70 条

[1] Syntheses and identification of the most abundant urinary type VI isoprostanes [J].

Adiyaman, M ;

Lawson, JA ;

FitzGerald, GA ;

Rokach, J .

TETRAHEDRON LETTERS, 1998, 39 (39) :7039-7042

[2] NEW EXTENSIONS OF BICYCLO[2.2.1]HEPTANE ROUTE TO PROSTAGLANDINS [J].

BINDRA, JS ;

GRODSKI, A ;

SCHAFF, TK ;

COREY, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (22) :7522-7523

[3] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].

BLANCHETTE, MA ;

CHOY, W ;

DAVIS, JT ;

ESSENFELD, AP ;

MASAMUNE, S ;

ROUSH, WR ;

SAKAI, T .

TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186

[4] A simple method for the selective deprotection of p-methoxybenzyl ethers by cerium(III) chloride heptahydrate and sodium iodide [J].

Cappa, A ;

Marcantoni, E ;

Torregiani, E ;

Bartoli, G ;

Bellucci, MC ;

Bosco, M ;

Sambri, L .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5696-5699

[5] INTRAMOLECULAR CYCLOADDITIONS OF KETENIMINIUM SALTS - A PRACTICAL ASYMMETRIC-SYNTHESIS OF PROSTAGLANDINS [J].

CHEN, LY ;

GHOSEZ, L .

TETRAHEDRON-ASYMMETRY, 1991, 2 (12) :1181-1184

[6] 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

[7]

Corey E.J., 1989, The Logic of Chemical Synthesis

[8] A NEW SYSTEM FOR CATALYTIC ENANTIOSELECTIVE REDUCTION OF ACHIRAL KETONES TO CHIRAL ALCOHOLS - SYNTHESIS OF CHIRAL ALPHA-HYDROXY ACIDS [J].

COREY, EJ ;

BAKSHI, RK .

TETRAHEDRON LETTERS, 1990, 31 (05) :611-614

[9] A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES - APPLICATIONS TO MULTISTEP SYNTHESES [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S ;

CHEN, CP ;

SINGH, VK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7925-7926

[10] SYNTHESIS OF NOVEL BICYCLIC PROSTAGLANDINS BY PHOTOCHEMICAL CYCLOADDITION REACTIONS [J].

CRABBE, P ;

GARCIA, GA ;

RIUS, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (08) :810-816

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