Enantioselective synthesis of cis-1,2-dialkyl substituted cyclopentanoid and isoprostane building blocks via 6-exo-trigonal radical cyclizations

被引：17

作者：

Zanoni, G ^{[1
]}

Re, S ^{[1
]}

Meriggi, A ^{[1
]}

Castronovo, F ^{[1
]}

Vidari, G ^{[1
]}

机构：

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

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 12期

关键词：

D O I：

10.1016/S0957-4166(01)00312-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Two different 6-exo-trigonal cyclizations of enantiomerically enriched 6-heptenyl radicals readily afforded versatile synthetic precursors of cis-1,2-dialkyl substituted cyclopentane derivatives. Starting from one of these intermediates, we accomplished an enantiospecific formal synthesis of two important isoprostanes, namely 15-F-2c-IsoP and ent-15-F-2c-IsoP. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1785 / 1792

页数：8

共 29 条

[1] PROSTAGLANDIN SYNTHESIS - DESIGN AND EXECUTION [J].

BREWSTER, D ;

MYERS, M ;

ORMEROD, J ;

OTTER, P ;

SMITH, ACB ;

SPINNER, ME ;

TURNER, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (22) :2796-2804

[2] SYNTHESIS OF PROSTAGLANDINS VIA A 2,3-DIOXABICYCLO[2.2.1]HEPTANE (ENDOPEROXIDE) INTERMEDIATE - STEREOCHEMICAL DIVERGENCE OF ENZYMATIC AND BIOMIMETIC CHEMICAL CYCLIZATION REACTIONS [J].

COREY, EJ ;

SHIMOJI, K ;

SHIH, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (21) :6425-6427

[3]

CURRAN DP, 1996, STEREOCHEMISTRY RADI, P77

[4] MCPBA OXIDATION OF BICYCLO[3.3.0]OCTANE-3,7-DIONE - AN EASY ENTRY TO A NEW FUNCTIONALIZED CYCLOPENTANOID BUILDING BLOCK [J].

GARLASCHELLI, L ;

VIDARI, G ;

ZANONI, G .

TETRAHEDRON, 1992, 48 (43) :9495-9502

[5] STEREOCHEMICAL CONSEQUENCE OF THE COUPLING OF LITHIUM DIMETHYLCUPRATE WITH A CYCLOPENTENYL ALLYLIC LACTONE - TOTAL SYNTHESIS OF DL-IRIDOMYRMECIN [J].

GRIECO, PA ;

SRINIVASAN, CV .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (12) :2591-2593

[6] Mechanism and applications of lithium amide-induced asymmetric rearrangements of 4-substituted and 4,4-disubstituted cyclopentene oxides to cyclopentenols [J].

Hodgson, DM ;

Gibbs, AR ;

Drew, MGB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (24) :3579-3590

[7] CONCISE RACEMIC AND HIGHLY ENANTIOSELECTIVE APPROACHES TO KEY INTERMEDIATES FOR THE SYNTHESES OF CARBOCYCLIC NUCLEOSIDES AND PSEUDO-RIBOFURANOSES - FORMAL SYNTHESES OF CARBOVIR [J].

HODGSON, DM ;

WITHERINGTON, J ;

MOLONEY, BA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (23) :3373-3378

[8] Total synthesis of 12-epi-PGF(2 alpha) [J].

Hwang, SW ;

Adiyaman, M ;

Khanapure, SP ;

Rokach, J .

TETRAHEDRON LETTERS, 1996, 37 (06) :779-782

[9] TOTAL SYNTHESIS OF 8-EPI-PGF(2-ALPHA) - A NOVEL STRATEGY FOR THE SYNTHESIS OF ISOPROSTANES [J].

HWANG, SW ;

ADIYAMAN, M ;

KHANAPURE, S ;

SCHIO, L ;

ROKACH, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (23) :10829-10830

[10] RADICAL REACTIONS IN NATURAL PRODUCT SYNTHESIS [J].

JASPERSE, CP ;

CURRAN, DP ;

FEVIG, TL .

CHEMICAL REVIEWS, 1991, 91 (06) :1237-1286

← 1 2 3 →