Staurosporine and ent-staurosporine: The first total syntheses, prospects for a regioselective approach, and activity profiles

被引：123

作者：

Link, JT

Raghavan, S

Gallant, M

Danishefsky, SJ

Chou, TC

Ballas, LM

机构：

[1] COLUMBIA UNIV,DEPT CHEM,NEW YORK,NY 10027

[2] MEM SLOAN KETTERING CANC CTR,BIOORGAN CHEM LAB,SLOAN KETTERING INST CANC RES,NEW YORK,NY 10021

[3] MEM SLOAN KETTERING CANC CTR,PROGRAM MOLEC PHARMACOL,SLOAN KETTERING INST CANC RES,NEW YORK,NY 10021

[4] YALE UNIV,DEPT CHEM,NEW HAVEN,CT 06511

[5] ELI LILLY & CO,SPHINX PHARMACEUT,DURHAM,NC 27707

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1996年 / 118卷 / 12期

关键词：

D O I：

10.1021/ja952907g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The total syntheses of staurosporine and ent-staurosporine have been achieved. Both glycosidic bonds were built from glycal precursors. The first was constructed by intermolecular coupling of an indole anion with a 1,2-anhydrosugar derived from an endo-glycal by direct epoxidation. The second bond was assembled from an exo-glycal by intramolecular iodoglycosylation.

引用

页码：2825 / 2842

页数：18

共 73 条

[31] K-252A, A POTENT INHIBITOR OF PROTEIN-KINASE-C FROM MICROBIAL ORIGIN
KASE, H
IWAHASHI, K
MATSUDA, Y
[J]. JOURNAL OF ANTIBIOTICS, 1986, 39 (08) : 1059 - 1065
[32] K-252 COMPOUNDS, NOVEL AND POTENT INHIBITORS OF PROTEIN-KINASE-C AND CYCLIC NUCLEOTIDE-DEPENDENT PROTEIN-KINASES
KASE, H
IWAHASHI, K
NAKANISHI, S
MATSUDA, Y
YAMADA, K
TAKAHASHI, M
MURAKATA, C
SATO, A
KANEKO, M
[J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1987, 142 (02) : 436 - 440
[33] A NEW INHIBITOR OF PROTEIN-KINASE-C, RK-1409 (7-OXOSTAUROSPORINE) .2. FERMENTATION, ISOLATION, PHYSICOCHEMICAL PROPERTIES AND STRUCTURE
KOSHINO, H
OSADA, H
ISONO, K
[J]. JOURNAL OF ANTIBIOTICS, 1992, 45 (02) : 195 - 198
[34] NAPHTHALENE COMPLEXES .5. ARENE EXCHANGE-REACTIONS IN NAPHTHALENECHROMIUM COMPLEXES
KUNDIG, EP
PERRET, C
SPICHIGER, S
BERNARDINELLI, G
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 286 (02) : 183 - 200
[35] GENERATION OF AND DIASTEREOSELECTIVE CYCLOADDITION REACTIONS TO ORTHO-QUINODIMETHANE TRICARBONYLCHROMIUM INTERMEDIATES
KUNDIG, EP
LERESCHE, J
[J]. TETRAHEDRON, 1993, 49 (25) : 5599 - 5615
[36] KUNEIDA T, 1987, TETRAHEDRON LETT, V28, P4185
[37] REGIOSELECTIVE IMIDE REDUCTION - AN ISSUE IN THE TOTAL SYNTHESIS OF STAUROSPORINE
LINK, JT
DANISHEFSKY, SJ
[J]. TETRAHEDRON LETTERS, 1994, 35 (49) : 9135 - 9138
[38] THE 1ST SYNTHESIS OF A FULLY FUNCTIONALIZED CORE STRUCTURE OF STAUROSPORINE - SEQUENTIAL INDOLYL GLYCOSIDATION BY ENDO AND EXO GLYCALS
LINK, JT
GALLANT, M
DANISHEFSKY, SJ
HUBER, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (09) : 3782 - 3783
[39] EPOXIDES DERIVED FROM PYRANOSYL DIENES - UNUSUALLY STABLE GLYCOSYL DONORS
LINK, JT
DANISHEFSKY, SJ
SCHULTE, G
[J]. TETRAHEDRON LETTERS, 1994, 35 (49) : 9131 - 9134
[40] TOTAL SYNTHESIS OF STAUROSPORINE AND ENT-STAUROSPORINE
LINK, JT
RAGHAVAN, S
DANISHEFSKY, SJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (01) : 552 - 553

← 1 2 3 4 5 6 7 8 →