Total synthesis of angucyclines.: Part 15:: A short synthesis of (±)-6-deoxybrasiliquinone B

被引：28

作者：

Krohn, K ^{[1
]}

Micheel, J ^{[1
]}

Zukowski, M ^{[1
]}

机构：

[1] Univ Paderborn, Facbereich Chem & Chem Tech, D-33098 Paderborn, Germany

来源：

TETRAHEDRON | 2000年 / 56卷 / 27期

关键词：

Diels-Alder reaction; boron triacetate; angucycline antibiotics; brasiliquinones; dimethyldioxirane oxidation;

D O I：

10.1016/S0040-4020(00)00398-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 6-deoxybrasiliquinones 2 and 14a were prepared by a boron triacetate mediated Diels-Alder reaction of juglone (9) with the crude mixture of ethoxy dienes 6 and 7. The primary non-aromatic Diels-Alder product 10 was isolated after reaction of the dienol 8 with 9. Dimethyldioxirane oxidation of 10 afforded the epoxide 11. (C) 2000 Published by Elsevier Science Ltd.

引用

页码：4753 / 4758

页数：6

共 31 条

[1] POTENTIAL PROPHYLACTIC ANTI-TUMOR ACTIVITY OF RETINYLIDENE 1,3-DIKETONES
ACTON, N
BROSSI, A
NEWTON, DL
SPORN, MB
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (07) : 805 - 809
[2] A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE
ADAM, W
BIALAS, J
HADJIARAPOGLOU, L
[J]. CHEMISCHE BERICHTE, 1991, 124 (10) : 2377 - 2377
[3] PALLADIUM-CATALYZED VINYLATION OF ALKYL VINYL ETHERS WITH ENOL TRIFLATES - A CONVENIENT SYNTHESIS OF 2-ALKOXY 1,3-DIENES
ANDERSSON, CM
HALLBERG, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) : 1502 - 1505
[4] DIELS-ALDER CYCLOADDITION OF JUGLONE DERIVATIVES - ELUCIDATION OF FACTORS INFLUENCING REGIOCHEMICAL CONTROL
BOECKMAN, RK
DOLAK, TM
CULOS, KO
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (22) : 7098 - 7100
[5] TOTAL SYNTHESIS OF THE ANGUCYCLINE ANTIBIOTICS URDAMYCINONE-B AND 104-2 VIA A COMMON SYNTHETIC INTERMEDIATE
BOYD, VA
SULIKOWSKI, GA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (32) : 8472 - 8473
[6] BROCKMANN H, 1963, Fortschr Chem Org Naturst, V21, P121
[7] Carreño MC, 2000, CHEM-EUR J, V6, P906
[8] Carreño MC, 1999, CHEM COMMUN, P817
[9] ELKHADEM HS, 1982, ANTHRACYCLINE ANTIBI
[10] GOH M, 1999, J ORG CHEM, V64, P7101

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