APPROACH TO ENOLONIUM EQUIVALENTS - APPLICATION TO A TOTAL SYNTHESIS OF (+/-)-PYRENOPHORIN

被引:70
作者
TROST, BM
GOWLAND, FW
机构
[1] Samuel M. McElvain Laboratories of Organic Chemistry, Department of Chemistry, University of Wisconsin-Madison, Madison
关键词
D O I
10.1021/jo01333a052
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Alkoxy-bearing allylic acetates can serve as substrates for palladium(0) catalysts under special conditions and thus constitute the equivalent of an enolonium and a vinylogous enolonium ion, a feature that has led to a formal synthesis of pyrenophorin and a synthesis of a fragment of zealeranone. Copyright © 1979, American Chemical Society. All rights reserved.
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页码:3448 / 3450
页数:3
相关论文
共 35 条
[1]  
BAKUZIS P, 1978, TETRAHEDRON LETT, P2371
[2]   ALPHA-METHOXYVINYLLITHIUM AND RELATED METALATED ENOL ETHERS - PRACTICAL REAGENTS FOR NUCLEOPHILIC ACYLATION [J].
BALDWIN, JE ;
HOFLE, GA ;
LEVER, OW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (22) :7125-7127
[3]   TOTAL SYNTHESIS OF MACROCYCLIC ANTIBIOTIC (+ OR -)-PYRENOPHORIN [J].
COLVIN, EW ;
PURCELL, TA ;
RAPHAEL, RA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (16) :1718-1722
[4]   ALPHA-ARYLATION OF ALPHA,BETA-UNSATURATED KETONES UTILIZATION OF ALPHA-EPOXYTOSYLHYDRAZONE FUNCTIONAL-GROUP AS A DELTA-2-ENONIUM SYNTHON [J].
FUCHS, PL .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (17) :2935-2937
[5]   NEW SYNTHESIS OF (+1-)-PYRENOPHORIN [J].
GERLACH, H ;
OERTLE, K ;
THALMANN, A .
HELVETICA CHIMICA ACTA, 1977, 60 (08) :2860-2865
[6]   METABOLIC PRODUCTS OF STEMPHYLIUM-RADICINUM .4. MINOR PRODUCTS [J].
GROVE, JF .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (12) :2261-&
[7]  
HERRMANN JL, 1973, TETRAHEDRON LETT, P4711
[8]   STEREOSPECIFIC SYNTHESIS OF HETEROATOM-SUBSTITUTED OLEFINS FROM ALPHA,BETA-EPOXYSILANES - PREPARATION OF VINYL BROMIDES, ENOL ACETATES, ENOL ETHERS, AND ENAMIDES [J].
HUDRLIK, PF ;
HUDRLIK, AM ;
RONA, RJ ;
MISRA, RN ;
WITHERS, GP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (06) :1993-1996
[9]   NEW MIXED OLEFIN COMPLEXES OF PALLADIUM (O) - STABILIZATION OF PD(O) STATE WITH A COMBINATION OF ELECTRON-DONATING AND ELECTRON-WITHDRAWING OLEFINS [J].
ITOH, K ;
UEDA, F ;
HIRAI, K ;
ISHII, Y .
CHEMISTRY LETTERS, 1977, (08) :877-880
[10]   TOTAL SYNTHESIS OF HUMULENE - STEREOSELECTIVE APPROACH [J].
KITAGAWA, Y ;
ITOH, A ;
HASHIMOTO, S ;
YAMAMOTO, H ;
NOZAKI, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (11) :3864-3867