A NEW HIGH-YIELD SEMISYNTHETIC APPROACH TO (20S)-9-NH2-CAMPTOTHECIN BASED ON A SEQUENCE OF PALLADIUM-CATALYZED REDUCTIONS

被引：13

作者：

CABRI, W ^{[1
]}

CANDIANI, I ^{[1
]}

ZARINI, F ^{[1
]}

PENCO, S ^{[1
]}

BEDESCHI, A ^{[1
]}

机构：

[1] PHARMACIA,PROC RES,I-20014 NERVIANO,ITALY

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 50期

关键词：

D O I：

10.1016/0040-4039(95)01939-F

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new 5-step synthesis of 9-NH2-Camptothecin starting from naturalCamptothecin is described. The approach, centred on a double palladium catalysed reduction of an arylsulfonate and a nitro group, has an overall yield consistently higher than the previously reported ones.

引用

页码：9197 / 9200

页数：4

共 19 条

[1] HECK REACTION ON ANTHRAQUINONE DERIVATIVES - LIGAND, SOLVENT, AND SALT EFFECTS
CABRI, W
CANDIANI, I
DEBERNARDINIS, S
FRANCALANCI, F
PENCO, S
SANTI, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) : 5796 - 5800
[2] PALLADIUM-CATALYZED REDUCTION OF ARYL SULFONATES - REDUCTION VERSUS HYDROLYSIS AND SELECTIVITY CONTROL
CABRI, W
DEBERNARDINIS, S
FRANCALANCI, F
PENCO, S
SANTI, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) : 350 - 353
[3] A NOVEL SYNTHESIS OF (+)-4-DEMETHOXYDAUNOMYCINONE
CABRI, W
DEBERNARDINIS, S
FRANCALANCI, F
PENCO, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (02): : 428 - 429
[4] COMINS DL, 1994, TETRAHEDRON LETT, V30, P5331
[5] SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-HYDROXY LACTONES BY SHARPLESS ASYMMETRIC DIHYDROXYLATIONS OF KETENE ACETALS, ENOL ETHERS, AND ENE LACTONES
CURRAN, DP
KO, SB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) : 6139 - 6141
[6] HORWITZ MS, 1971, BIOCHEM BIOPH RES CO, V45, P723
[7] HORWITZ S, 1973, CANCER RES, P2834
[8] CAMPTOTHECIN - CHEMISTRY, BIOGENESIS AND MEDICINAL CHEMISTRY
HUTCHINSON, CR
[J]. TETRAHEDRON, 1981, 37 (06) : 1047 - 1065
[9] SYNTHESIS OF WATER-SOLUBLE (AMINOALKYL)CAMPTOTHECIN ANALOGS - INHIBITION OF TOPOISOMERASE-I AND ANTITUMOR-ACTIVITY
KINGSBURY, WD
BOEHM, JC
JAKAS, DR
HOLDEN, KG
HECHT, SM
GALLAGHER, G
CARANFA, MJ
MCCABE, FL
FAUCETTE, LF
JOHNSON, RK
HERTZBERG, RP
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (01) : 98 - 107
[10] POTMESIL M, 1994, CANCER RES, V54, P1431

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