PREPARATION OF THE A-RING OF NEOCARZINOSTATIN AND KEDARCIDIN CHROMOPHORES VIA A STEREOCONTROLLED BASE-MEDIATED ISOMERIZATION REACTION

被引：17

作者：

CADDICK, S

KHAN, S

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1995年 / 19期

关键词：

D O I：

10.1039/c39950001971

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new base promoted isomerisation of 6-(1,1-dimethylethoxy)-2H-pyran-3-one to 4-(1,1-dimethylethoxy)-5-hydroxy-2-cyclopentenone is used in the preparation of 2-bromo-5-[(1,1 dimethylethyl)dimethylsilyloxy]-4-hydroxy-2-cyclopentenone, a potential intermediate for use in the synthesis of Neocarzinostatin and Kedarcidin chromophores.

引用

页码：1971 / 1972

页数：2

共 28 条

[1] SYNTHESIS OF METHYL 2,3-DIDEOXY-DL-ALK-2-ENOPYRANOSIDES FROM FURAN COMPOUNDS - GENERAL APPROACH TO TOTAL SYNTHESIS OF MONOSACCHARIDES
ACHMATOWICZ, O
BUKOWSKI, P
SZECHNER, B
ZWIERZCHOWSKA, Z
ZAMOJSKI, A
[J]. TETRAHEDRON, 1971, 27 (10) : 1973 - +
[2] THE STRUCTURE OF NEOCARZINOSTATIN CHROMOPHORE POSSESSING A NOVEL BICYCLO-[7,3,0]DODECADIYNE SYSTEM
EDO, K
MIZUGAKI, M
KOIDE, Y
SETO, H
FURIHATA, K
OTAKE, N
ISHIDA, N
[J]. TETRAHEDRON LETTERS, 1985, 26 (03) : 331 - 334
[3] THE CONVERSION OF CARBOHYDRATE-DERIVATIVES INTO FUNCTIONALIZED CYCLOHEXANES AND CYCLOPENTANES
FERRIER, RJ
MIDDLETON, S
[J]. CHEMICAL REVIEWS, 1993, 93 (08) : 2779 - 2831
[4] MECHANISM OF NEOCARZINOSTATIN ACTION - ROLE OF DNA MICROSTRUCTURE IN DETERMINATION OF CHEMISTRY OF BISTRANDED OXIDATIVE DAMAGE
GOLDBERG, IH
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (07) : 191 - 198
[5] CHEMOENZYMATIC SYNTHESIS OF TRANS-4,5-DIHYDROXYCYCLOPENT-2-ENONES - CONVERSION TO D-1-DEOXYNOJIRIMYCIN
JOHNSON, CR
NERURKAR, BM
GOLEBIOWSKI, A
SUNDRAM, H
ESKER, JL
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (11) : 1139 - 1140
[6] A RING CONTRACTION OF 6-ALKOXY-2,3-DIHYDRO-6H-PYRAN-3-ONES TO POLYFUNCTIONALIZED CYCLOPENTENONES
KOLB, HC
HOFFMANN, HMR
[J]. TETRAHEDRON, 1990, 46 (15) : 5127 - 5144
[7] A TOTAL SYNTHESIS OF RACEMIC AND OPTICALLY-ACTIVE TERREIN (TRANS-4,5-DIHYDROXY-3-[(E)-1-PROPENYL]-2-CYCLOPENTEN-1-ONE)
KOLB, HC
HOFFMANN, HMR
[J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (04) : 237 - 250
[8] KEDARCIDIN, A NEW CHROMOPROTEIN ANTITUMOR ANTIBIOTIC - STRUCTURE ELUCIDATION OF KEDARCIDIN CHROMOPHORE
LEET, JE
SCHROEDER, DR
HOFSTEAD, SJ
GOLIK, J
COLSON, KL
HUANG, S
KLOHR, SE
DOYLE, TW
MATSON, JA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (20) : 7946 - 7948
[9] A GENERAL STRATEGY USING ETA-CO-2(2)(CO)(6) ACETYLENE COMPLEXES FOR THE SYNTHESIS OF THE ENEDIYNE ANTITUMOR AGENTS ESPERAMICIN, CALICHEAMICIN, DYNEMICIN AND NEOCARZINOSTATIN
MAGNUS, P
[J]. TETRAHEDRON, 1994, 50 (05) : 1397 - 1418
[10] IMPROVED PROCEDURE FOR THE SYNTHESIS OF 6-ALKOXY-2,3-DIHYDRO-6H-PYRAN-3-ONES (2,3-DIDEOXY-DL-PENT-2-ENOPYRANOS-4-ULOSES) - NEAT CONVERSION INTO POLYFUNCTIONALIZED CYCLOPENTENONES
MUCHA, B
HOFFMANN, HMR
[J]. TETRAHEDRON LETTERS, 1989, 30 (34) : 4489 - 4492

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