A HIGHLY CONCISE SYNTHESIS OF LAVENDAMYCIN METHYL-ESTER

被引：53

作者：

BEHFOROUZ, M

GU, ZX

CAI, W

HORN, MA

AHMADIAN, M

机构：

[1] Department of Chemistry, Ball State University, Muncie

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 25期

关键词：

D O I：

10.1021/jo00077a032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lavendamycin methyl ester (2), an antitumor antibiotic, was synthesized by a practical and short route in an excellent overall yield of 33% from known starting materials. Pictet-Spengler condensation of 7-acetamido-2-formylquinoline-5,8-dione (4) with the methyl ester of (2RS,3SR)-beta-methyltryptophan (5) followed by hydrolysis afforded 2. Aldehyde 4 was prepared by the oxidation of 7-acetamido-2-methylquinoline-5,8-dione (9). Dione 9 was obtained via the Diels-Alder condensation of the novel 1-[(tert-butyldimethylsilyl)oxy]-2-methyl-1-aza-1,3-butadiene (7) with 2-acetamido-6-bromobenzene-1,4-dione (8).

引用

页码：7089 / 7091

页数：3

共 30 条

[1] ISOLATION OF LAVENDAMYCIN A NEW ANTIBIOTIC FROM STREPTOMYCES-LAVENDULAE
BALITZ, DM
BUSH, JA
BRADNER, WT
DOYLE, TW
OHERRON, FA
NETTLETON, DE
[J]. JOURNAL OF ANTIBIOTICS, 1982, 35 (03) : 259 - 265
[2] BETA-CARBOLINES DERIVED FROM BETA-METHYLTRYPTOPHAN AND A STEREOSELECTIVE SYNTHESIS OF 2RS,3SR)-BETA-METHYLTRYPTOPHAN METHYL-ESTER
BEHFOROUZ, M
ZARRINMAYEH, H
OGLE, ME
RIEHLE, TJ
BELL, FW
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1988, 25 (06) : 1627 - 1632
[3] Boger D. L., 1987, HETERO DIELS ALDER M
[4] BOGER DL, 1990, B SOC CHIM BELG, V99, P599
[5] TOTAL SYNTHESIS OF LAVENDAMYCIN METHYL-ESTER
BOGER, DL
DUFF, SR
PANEK, JS
YASUDA, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) : 5790 - 5795
[6] STREPTONIGRIN AND LAVENDAMYCIN PARTIAL STRUCTURES - PROBES FOR THE MINIMUM, POTENT PHARMACOPHORE OF STREPTONIGRIN, LAVENDAMYCIN, AND SYNTHETIC QUINOLINE-5,8-DIONES
BOGER, DL
YASUDA, M
MITSCHER, LA
DRAKE, SD
KITOS, PA
THOMPSON, SC
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (10) : 1918 - 1928
[7] BOGER DL, 1991, COMPREHENSIVE ORGANI, V5, P451
[8] BOGER DL, 1989, STRATEGIES TACTICS O, V2, P2
[9] EXPEDIENT SYNTHESIS OF MONO-TRIMETHYLSILYL HYDROXYLAMINE AND BIS-TRIMETHYLSILYL HYDROXYLAMINE
BOTTARO, JC
BEDFORD, CD
DODGE, A
[J]. SYNTHETIC COMMUNICATIONS, 1985, 15 (14) : 1333 - 1335
[10] STRUCTURE DETERMINATION OF LAVENDAMYCIN - A NEW ANTI-TUMOR ANTIBIOTIC FROM STREPTOMYCES-LAVENDULAE
DOYLE, TW
BALITZ, DM
GRULICH, RE
NETTLETON, DE
GOULD, SJ
TANN, CH
MOEWS, AE
[J]. TETRAHEDRON LETTERS, 1981, 22 (46) : 4595 - 4598

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