The first stereospecific synthesis of michellamine B

被引：40

作者：

Hobbs, PD ^{[1
]}

Upender, V ^{[1
]}

Liu, JW ^{[1
]}

Pollart, DJ ^{[1
]}

Thomas, DW ^{[1
]}

Dawson, MI ^{[1
]}

机构：

[1] SRI INT,BIOORGAN CHEM LAB,MENLO PK,CA 94025

来源：

CHEMICAL COMMUNICATIONS | 1996年 / 08期

关键词：

D O I：

10.1039/cc9960000923

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The dimeric alkaloid michellamine B is synthesized stereospecifically by the palladium-catalysed cross-coupling of the 6'-naphthaleneboronic acid of the tetrabenzylated derivative of korupensamine A and the 6'-bromo analogue of the tetrabenzylated derivative of korupensamine B, both of which are prepared by total synthesis.

引用

收藏

页码：923 / 924

页数：2

相关论文

共 16 条

[1] ANTI-HIV MICHELLAMINES FROM ANCISTROCLADUS-KORUPENSIS [J].

BOYD, MR ;

HALLOCK, YF ;

MANFREDI, KP ;

BLUNT, JW ;

MCMAHON, JB ;

BUCKHEIT, RW ;

BRINGMANN, G ;

SCHAFFER, M ;

CRAGG, GM ;

THOMAS, DW ;

JATO, JG ;

CARDELLINA, JH .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (12) :1740-1745

[2] THE ABSOLUTE-CONFIGURATION OF MICHELLAMINE-B, A DIMERIC, ANTI-HIV-ACTIVE NAPHTHYLISOQUINOLINE ALKALOID [J].

BRINGMANN, G ;

ZAGST, R ;

SCHAFFER, M ;

HALLOCK, YF ;

CARDELLINA, JH ;

BOYD, MR .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (08) :1190-1191

[3] ACETOGENIC ISOQUINOLINE ALKALOIDS .69. BIOMIMETIC OXIDATIVE DIMERIZATION OF KORUPENSAMINE A - COMPLETION OF THE FIRST TOTAL SYNTHESIS OF MICHELLAMINE-A, MICHELLAMINE-B, AND MICHELLAMINE-C [J].

BRINGMANN, G ;

HARMSEN, S ;

HOLENZ, J ;

GEUDER, T ;

GOTZ, R ;

KELLER, PA ;

WALTER, R ;

HALLOCK, YF ;

CARDELLINA, JH ;

BOYD, MR .

TETRAHEDRON, 1994, 50 (32) :9643-9648

[4] ACETOGENIC ISOQUINOLINE ALKALOIDS .66. FIRST TOTAL SYNTHESIS OF KORUPENSAMINE-A AND KORUPENSAMINE-B [J].

BRINGMANN, G ;

GOTZ, R ;

KELLER, PA ;

WALTER, R ;

HENSCHEL, P ;

SCHAFFER, M ;

STABLEIN, M ;

KELLY, TR ;

BOYD, MR .

HETEROCYCLES, 1994, 39 (02) :503-508

[5] REMOVAL OF BENZYL-TYPE PROTECTING GROUPS FROM PEPTIDES BY CATALYTIC TRANSFER HYDROGENATION WITH FORMIC-ACID [J].

ELAMIN, B ;

ANANTHARAMAIAH, GM ;

ROYER, GP ;

MEANS, GE .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (19) :3442-3444

[6] KORUPENSAMINES-A-D, NOVEL ANTIMALARIAL ALKALOIDS FROM ANCISTROCLADUS-KORUPENSIS [J].

HALLOCK, YF ;

MANFREDI, KP ;

BLUNT, JW ;

CARDELLINA, JH ;

SCHAFFER, M ;

GULDEN, KP ;

BRINGMANN, G ;

LEE, AY ;

CLARDY, J ;

FRANCOIS, G ;

BOYD, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6349-6355

[7] TOTAL SYNTHESIS OF MICHELLAMINES A-C - IMPORTANT ANTI-HIV AGENTS [J].

HOYE, TR ;

CHEN, MZ ;

MI, L ;

PRIEST, OP .

TETRAHEDRON LETTERS, 1994, 35 (47) :8747-8750

[8] CONVERGENT TOTAL SYNTHESIS OF THE MICHELLAMINES [J].

KELLY, TR ;

GARCIA, A ;

LANG, FR ;

WALSH, JJ ;

BHASKAR, KV ;

BOYD, MR ;

GOTZ, R ;

KELLER, PA ;

WALTER, R ;

BRINGMANN, G .

TETRAHEDRON LETTERS, 1994, 35 (41) :7621-7624

[9] NOVEL ALKALOIDS FROM THE TROPICAL PLANT ANCISTROCLADUS-ABBREVIATUS INHIBIT CELL KILLING BY HIV-1 AND HIV-2 [J].

MANFREDI, KP ;

BLUNT, JW ;

CARDELLINA, JH ;

MCMAHON, JB ;

PANNELL, LL ;

CRAGG, GM ;

BOYD, MR .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (12) :3402-3405

[10] MICHELLAMINE-B, A NOVEL PLANT ALKALOID, INHIBITS HUMAN IMMUNODEFICIENCY VIRUS-INDUCED CELL-KILLING BY AT LEAST 2 DISTINCT MECHANISMS [J].

MCMAHON, JB ;

CURRENS, MJ ;

GULAKOWSKI, RJ ;

BUCKHEIT, RW ;

LACKMANSMITH, C ;

HALLOCK, YF ;

BOYD, MR .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1995, 39 (02) :484-488