ENANTIOSPECIFIC SYNTHESIS OF AN AZIRIDINOBENZOAZOCINONE, AN ADVANCED INTERMEDIATE CONTAINING THE CORE NUCLEUS OF FR900482 AND FK973

被引：64

作者：

JONES, RJ ^{[1
]}

RAPOPORT, H ^{[1
]}

机构：

[1] UNIV CALIF BERKELEY,DEPT CHEM,BERKELEY,CA 94720

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 04期

关键词：

D O I：

10.1021/jo00291a010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A route to the enantiospecific synthesis of the aziridinobenzohexahydroazocine ketone 14, containing the core nucleus of FR900482 and FK973, has been developed. It consists of coupling the two key intermediates, sulfon-anilide 7 and methyl (2S,3S)-2,3-aziridino-4-hydroxy-butyrate 12, prepared from vinylglycine, followed by cyclization to the azocinone 14. © 1990, American Chemical Society. All rights reserved.

引用

页码：1144 / 1146

页数：3

共 14 条

[1] SYNTHESIS OF OPTICALLY PURE PIPECOLATES FROM L-ASPARAGINE - APPLICATION TO THE TOTAL SYNTHESIS OF (+)-APOVINCAMINE THROUGH AMINO-ACID DECARBONYLATION AND IMINIUM ION CYCLIZATION
CHRISTIE, BD
RAPOPORT, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (08) : 1239 - 1246
[2] OXIDO ALCOHOLS AND KETOXIDES
FIESER, LF
GOTO, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (07) : 1693 - 1697
[3] A NEW ANTITUMOR ANTIBIOTIC, FR-900482 .4. HEMATOLOGICAL TOXICITY IN MICE
HIRAI, O
SHIMOMURA, K
MIZOTA, T
MATSUMOTO, S
MORI, J
KIKUCHI, H
[J]. JOURNAL OF ANTIBIOTICS, 1987, 40 (05) : 607 - 611
[4] IWAMI M, 1987, J ANTIBIOT, V440, P589
[5] A NEW ANTITUMOR ANTIBIOTIC, FR-900482 .2. PRODUCTION, ISOLATION, CHARACTERIZATION AND BIOLOGICAL-ACTIVITY
KIYOTO, S
SHIBATA, T
YAMASHITA, M
KOMORI, T
OKUHARA, M
TERANO, H
KOHSAKA, M
AOKI, H
IMANAKA, H
[J]. JOURNAL OF ANTIBIOTICS, 1987, 40 (05) : 594 - 599
[6] A NEW ANTITUMOR ANTIBIOTIC, FR-900482 .5. INTERSTRAND DNA-DNA CROSS-LINKS IN L1210 CELLS
MASUDA, K
NAKAMURA, T
SHIMOMURA, K
SHIBATA, T
TERANO, H
KOHSAKA, M
[J]. JOURNAL OF ANTIBIOTICS, 1988, 41 (10) : 1497 - 1499
[7] MASUDA K, 1908, CANCER RES, V48, P5172
[8] AMINOBENZOIC ACID DIURETICS .7. 3-SUBSTITUTED 4-PHENYL-5-SULFAMOYLBENZOIC, 4-ARYLCARBONYL-5-SULFAMOYLBENZOIC, AND 4-ARYLMETHYL-5-SULFAMOYLBENZOIC ACIDS AND RELATED COMPOUNDS
NIELSEN, OBT
BRUUN, H
BRETTING, C
FEIT, PW
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1975, 18 (01) : 41 - 50
[9] ROUTES TO MITOMYCINS - CHIROSPECIFIC SYNTHESIS OF AZIRIDINOMITOSENES
SHAW, KJ
LULY, JR
RAPOPORT, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (23) : 4515 - 4523
[10] A NEW ANTITUMOR ANTIBIOTIC, FR-900482 .3. ANTITUMOR-ACTIVITY IN TRANSPLANTABLE EXPERIMENTAL-TUMORS
SHIMOMURA, K
HIRAI, O
MIZOTA, T
MATSUMOTO, S
MORI, J
SHIBAYAMA, F
KIKUCHI, H
[J]. JOURNAL OF ANTIBIOTICS, 1987, 40 (05) : 600 - 606

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