Total synthesis of (±)-brasiliquinone B

被引：29

作者：

Patil, ML ^{[1
]}

Borate, HB ^{[1
]}

Ponde, DE ^{[1
]}

Deshpande, VH ^{[1
]}

机构：

[1] Natl Chem Lab, Pune 411008, Maharashtra, India

来源：

TETRAHEDRON | 2002年 / 58卷 / 33期

关键词：

antitumor; antibiotics; Friedel-Crafts reaction; regiospecificity;

D O I：

10.1016/S0040-4020(02)00740-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of (+/-)-brasiliquinone B has been achieved via a Friedel-Crafts alkylation approach. In contrast, a Friedel-Crafts acylation approach for the synthesis of (+/-)-brasiliquinone B resulted in formation of A ring aromatized tetracyclic products. (C) 2002 Published by Elsevier Science Ltd.

引用

页码：6615 / 6620

页数：6

共 13 条

[1] NATURALLY OCCURRING QUINONES .26. SYNTHESIS OF TETRANGULOL (1,8-DIHYDROXY-3-METHYLBENZ[A]ANTHRACENE-7,12-QUINONE)
BROWN, PM
THOMSON, RH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (09): : 997 - 1000
[2] DANN M, 1965, ANTIMICROB AGENTS CH, P832
[3] Trihydroxy-methyl-anthraquinones I
Graves, GD
Adams, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1923, 45 : 2439 - 2455
[4] ANTHRACYCLINES AND RELATED SUBSTANCES .2. EFFICIENT AND REGIOSPECIFIC SYNTHESIS OF DL-7,9-DIDEOXYDAUNOMYCINONE
KIM, KS
VANOTTI, E
SUARATO, A
JOHNSON, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (09) : 2483 - 2484
[5] Total synthesis of angucyclines.: Part 15:: A short synthesis of (±)-6-deoxybrasiliquinone B
Krohn, K
Micheel, J
Zukowski, M
[J]. TETRAHEDRON, 2000, 56 (27) : 4753 - 4758
[6] Kunstmann M. P., 1966, J ORG CHEM, V31, P2920
[7] A concise total synthesis of brasiliquinones B and C and 3-deoxyrabelomycin
Mal, D
Roy, HN
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (21): : 3167 - 3171
[8] MILLER DG, 1976, TETRAHEDRON LETT, P1637
[9] Nemoto A, 1997, J ANTIBIOT, V50, pC1
[10] Brasiliquinones A, B and C, new benz[alpha]anthraquinone antibiotics from Nocardia brasiliensis .1. Producing strain, isolation and biological activities of the antibiotics
Nemoto, A
Tanaka, Y
Karasaki, Y
Komaki, H
Yazawa, K
Mikami, Y
Tojo, T
Kadowaki, K
Tsuda, M
Kobayashi, J
[J]. JOURNAL OF ANTIBIOTICS, 1997, 50 (01) : 18 - 21

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