SYNTHETIC ROUTES TO (+/-)-DAUNOMYCINONE - ELABORATION OF THE HYDROXY-KETONE GROUP FROM AN ALPHA-TETRALONE DERIVATIVE, AND SELECTIVE METHYLATION OF THE C(4)-HYDROXY GROUP USING DIAZOMETHANE

被引：34

作者：

BLADE, RJ ^{[1
]}

HODGE, P ^{[1
]}

机构：

[1] UNIV LANCASTER, DEPT CHEM, LANCASTER LA1 4YQ, LANCASHIRE, ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1979年 / 02期

关键词：

D O I：

10.1039/c39790000085

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A 12 step synthetic route to (.+-.)-daunomycinone [an antineoplastic drug] is described which uses Friedel-Crafts reactions to assemble the ring system; (-)-carminomycinone reacts with diazomethane to give (+)-daunomycinone.

引用

页码：85 / 86

页数：2

共 12 条

[1] GLEIM RD, 1976, TETRAHEDRON LETT, P3385
[2] VERSUCHE ZUR SYNTHESE VON VERBINDUNGEN DER STEROIDREIHE .4. EINE VERBESSERTE SYNTHESE DES 7-KETO-1,4-DIMETHOXY-13-METHYL-5,6,7,9,10,13-HEXAHYDRO-PHENANTHRENS
GROB, CA
JUNDT, W
[J]. HELVETICA CHIMICA ACTA, 1952, 35 (06) : 2111 - 2115
[3] HARWOOD LM, 1978, J CHEM SOC CHEM COMM, P712, DOI 10.1039/c39780000712
[4] TOTAL SYNTHESIS OF RHODOMYCIN AGLYCONES
KENDE, AS
TSAY, YG
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (05) : 140 - 141
[5] KENDE AS, 1977, TETRAHEDRON LETT, P3537
[6] TOTAL SYNTHESIS OF (+ OR -)-DAUNOMYCINONE AND (+ OR -)-CARMINOMYCINONE
KENDE, AS
TSAY, YG
MILLS, JE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (07) : 1967 - 1969
[7] SYNTHESIS OF 6-HYDROXY-1,3,4,5-TETRAHYDROBENZ [CD] INDOLE
MOORE, JA
RAHM, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (04) : 1109 - +
[8] SYNTHETIC APPROACHES TO ADRIAMYCIN - DEGRADATION OF DAUNORUBICIN TO NON-ASYMMETRIC TETRACYCLIC KETONE AND REFUNCTIONALIZATION OF A-RING TO ADRIAMYCIN
SMITH, TH
FUJIWARA, AN
HENRY, DW
LEE, WW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (07) : 1969 - 1971
[9] THOMSON RH, 1971, NATURALLY OCCURRING, pCH6
[10] ANTITUMOR AGENTS .13. ISOLATION AND ABSOLUTE-CONFIGURATION OF CARMINOMYCIN-I FROM STREPTOSPORANGIUM SP
WANI, MC
TAYLOR, HL
WALL, ME
MCPHAIL, AT
ONAN, KD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (20) : 5955 - 5956

← 1 2 →