A DIRECT SYNTHESIS OF RACEMIC DEMETHOXYAFLATOXIN-B2

被引：29

作者：

KRAUS, GA ^{[1
]}

JOHNSTON, BE ^{[1
]}

APPLEGATE, JM ^{[1
]}

机构：

[1] IOWA STATE UNIV SCI & TECHNOL,PROGRAM TOXICOL,AMES,IA 50011

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 19期

关键词：

D O I：

10.1021/jo00019a042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aflatoxin analogue 19 was prepared by a direct sequence involving a novel silver-mediated cyclization to 12, the Michael addition of 16 with 17, and the oxidation of the Michael addition adduct. The overall yield of this six-step route is approximately 11%. The pathway is a flexible one that will permit the synthesis of analogues for toxicological analysis.

引用

页码：5688 / 5691

页数：4

共 12 条

[1] THERMAL 1,5-REARRANGEMENT OF A SILYL GROUP FROM OXYGEN TO CARBON
ANDERSON, G
FEUTRILL, GI
READ, RW
CAMERON, DW
[J]. TETRAHEDRON LETTERS, 1981, 22 (43) : 4347 - 4348
[2] BUCHI G, 1981, J AM CHEM SOC, V103, P3497, DOI 10.1021/ja00402a039
[3] SYNTHESES OF TETRAHYDROFURO[2,3-B]BENZOFURANS - A SYNTHESIS OF (H-AFLATOXIN-B2
CASTELLINO, AJ
RAPOPORT, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (07) : 1006 - 1011
[4] MANGANESE(III)-BASED OXIDATIVE FREE-RADICAL TANDEM AND TRIPLE CYCLIZATIONS
DOMBROSKI, MA
KATES, SA
SNIDER, BB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (07) : 2759 - 2767
[5] HORNE S, 1990, J CHEM SOC CHEM COMM, V39
[6] OXIDATIVE COUPLING OF CARBON ACID COMPOUNDS BY MEANS OF AG2O
ITO, Y
FUJII, S
KONOIKE, T
SAEGUSA, T
[J]. SYNTHETIC COMMUNICATIONS, 1976, 6 (06) : 429 - 433
[7] Kosower E.M., 1963, J ORG CHEM, V28
[8] AN APPROACH TO AFLATOXINS USING TYPE-II PHOTOCYCLIZATION REACTIONS
KRAUS, GA
THOMAS, PJ
SCHWINDEN, MD
[J]. TETRAHEDRON LETTERS, 1990, 31 (13) : 1819 - 1822
[9] ORGANOSELENIUM CHEMISTRY - CONVERSION OF KETONES TO ENONES BY SELENOXIDE SYN ELIMINATION
REICH, HJ
RENGA, JM
REICH, IL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (19) : 5434 - 5447
[10] Schuda P. F., 1980, TOP CURR CHEM, P75

← 1 2 →