Short, enantioselective total synthesis of Stephacidin A

被引：129

作者：

Baran, PS ^{[1
]}

Guerrero, CA ^{[1
]}

Ambhaikar, NB ^{[1
]}

Hafensteiner, BD ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 04期

关键词：

alkaloids; cascade reactions; indoles; natural products; total synthesis;

D O I：

10.1002/anie.200461864

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise route to the heptacyclic indole alkaloid stephacidin A (1) includes a simple method for the gram-scale synthesis of substituted tryptophans, a remarkable indole annulation, and the first enolate coupling of an amide to an ester. This synthesis secures the relative configuration of the natural product and paves a potential path to several of its congeners.

引用

页码：606 / 609

页数：4

共 41 条

[1] Concise synthesis of the core bicyclo[2.2.2]diazaoctane ring common to asperparaline, paraherquamide, and stephacidin alkaloids
Adams, LA
Gray, CR
Williams, RM
[J]. TETRAHEDRON LETTERS, 2004, 45 (23) : 4489 - 4493
[2] ENTRY INTO 6-METHOXY-D(+)-TRYPTOPHANS - STEREOSPECIFIC SYNTHESIS OF 1-BENZENESULFONYL-6-METHOXY-D(+)-TRYPTOPHAN ETHYL-ESTER
ALLEN, MS
HAMAKER, LK
LALOGGIA, AJ
COOK, JM
[J]. SYNTHETIC COMMUNICATIONS, 1992, 22 (14) : 2077 - 2102
[3] Direct coupling of pyrroles with carbonyl compounds: Short enantioselective synthesis of (S)-Ketorolac
Baran, PS
Richter, JM
Lin, DW
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (04) : 609 - 612
[4] Direct coupling of indoles with carbonyl compounds: Short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families
Baran, PS
Richter, JM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) : 7450 - 7451
[5] BARAN PS, 2005, ANGEW CHEM, V117, P615
[6] STUDIES IN RELATION TO BIOSYNTHESIS .42. STRUCTURAL ELUCIDATION AND SOME ASPECTS OF BIOSYNTHESIS OF BREVIANAMIDES-A AND BREVIANAMIDES-E
BIRCH, AJ
WRIGHT, JJ
[J]. TETRAHEDRON, 1970, 26 (10) : 2329 - &
[7] CATECHOL BORON HALIDES - MILD AND SELECTIVE REAGENTS FOR CLEAVAGE OF COMMON PROTECTING GROUPS
BOECKMAN, RK
POTENZA, JC
[J]. TETRAHEDRON LETTERS, 1985, 26 (11) : 1411 - 1414
[8] SYNTHESIS OF ARISTOTELINE-TYPE ALKALOIDS .2. THE STRUCTURE OF NEOHOBARTINE, A SIDE PRODUCT OF THE HOBARTINE-ARISTOTELINE TRANSFORMATION
BORSCHBERG, HJ
[J]. HELVETICA CHIMICA ACTA, 1984, 67 (07) : 1878 - 1882
[9] THERMAL REACTIONS OF ALKYL N-CARBOMETHOXYSULFAMATE ESTERS
BURGESS, EM
PENTON, HR
TAYLOR, EA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (01) : 26 - 31
[10] Syntheses of indoles via a palladium-catalyzed annulation between iodoanilines and ketones
Chen, CY
Lieberman, DR
Larsen, RD
Verhoeven, TR
Reider, PJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (09) : 2676 - 2677

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