EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .14. AN INTERMEDIATE FOR THE SYNTHESIS OF VINEOMYCINS

被引：15

作者：

CAMBIE, RC ^{[1
]}

HOWE, TA ^{[1
]}

PAUSLER, MG ^{[1
]}

RUTLEDGE, PS ^{[1
]}

WOODGATE, PD ^{[1
]}

机构：

[1] UNIV AUCKLAND, DEPT CHEM, AUCKLAND, NEW ZEALAND

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1987年 / 40卷 / 06期

关键词：

D O I：

10.1071/CH9871063

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Anthrarufin (4) has been converted by a high-yielding route involving sequential reductive Claisen rearrangements into 1-acetoxy-5-methoxy-9,10-dioxo-6-(2''-oxopropyl)-9,10-dihydroanthracene-2-carbaldehyde (3), an intermediate which is suitable for the synthesis of vineomycins. The thermal Claisen rearrangements of some allyl ethers of 1,5-dihydroxyanthraquinone have been examined.

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页码：1063 / 1072

页数：10

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共 14 条

[1] EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .8. FUNCTIONALIZATION OF HYDROXYANTHRAQUINONES BY REDUCTIVE CLAISEN REARRANGEMENTS [J].

BODDY, IK ;

BONIFACE, PJ ;

CAMBIE, RC ;

CRAW, PA ;

HUANG, ZD ;

LARSEN, DS ;

MCDONALD, H ;

RUTLEDGE, PS ;

WOODGATE, PD .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1984, 37 (07) :1511-1529

[2] EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .12. PREPARATION OF A SUBSTITUTED ISOBENZOFURAN FROM AN ANTHRADIFURAN [J].

BODDY, IK ;

CAMBIE, RC ;

RUTLEDGE, PS ;

WOODGATE, PD .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1986, 39 (12) :2075-2088

[3] EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .10. A SYNTHESIS OF (+/-)-4-DEMETHOXYDAUNOMYCINONE [J].

CAMBIE, RC ;

LARSEN, DS ;

RICKARD, CEF ;

RUTLEDGE, PS ;

WOODGATE, PD .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1986, 39 (03) :487-502

[4] A CLAISEN REARRANGEMENT ROUTE TO THE VINEOMYCINS [J].

CAMBIE, RC ;

PAUSLER, MG ;

RUTLEDGE, PS ;

WOODGATE, PD .

TETRAHEDRON LETTERS, 1985, 26 (43) :5341-5342

[5] EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .6. CLAISEN REARRANGEMENTS OF 1,4-BIS(PROP-2'-ENYLOXY)ANTHRAQUINONE [J].

CAMBIE, RC ;

DUNLOP, MG ;

NOALL, WI ;

RUTLEDGE, PS ;

WOODGATE, PD .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1981, 34 (05) :1079-1084

[6] EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .5. DOUBLE CLAISEN REARRANGEMENT OF 1,4-BIS(ALLYLOXY)ANTHRAQUINONES [J].

CAMBIE, RC ;

ZHENDONG, H ;

NOALL, WI ;

RUTLEDGE, PS ;

WOODGATE, PD .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1981, 34 (04) :819-828

[7] TOTAL SYNTHESIS OF VINEOMYCINONE-B2 METHYL-ESTER [J].

DANISHEFSKY, SJ ;

UANG, BJ ;

QUALLICH, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (05) :1285-1293

[8] PHOSPHORUS PENTOXIDE-METHANESULFONIC ACID - CONVENIENT ALTERNATIVE TO POLYPHOSPHORIC ACID [J].

EATON, PE ;

CARLSON, GR ;

LEE, JT .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (23) :4071-4073

[9]

HUANG ZD, 1981, THESIS U AUCKLAND

[10]

IMAMURA N, 1981, CHEM PHARM BULL, V29, P1788