Total Synthesis of Kapakahine E and F

被引：61

作者：

Espejo, Vinson R. ^{[1
]}

Rainier, Jon D. ^{[1
]}

机构：

[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 09期

基金：

美国国家科学基金会;

关键词：

SPONGE CRIBROCHALINA-OLEMDA; FRIEDEL-CRAFTS ALKYLATION; MARINE SPONGE; AMINO-ACID; ORGANOZINC REAGENTS; DERIVATIVES; INDOLES; REACTIVITY; CHEMISTRY; ANALOGS;

D O I：

10.1021/ol100672z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of the cyclic peptides kapakahine E and F using bromopyrroloindoline heterodimerization reactions, indoline to a-carboline rearrangements, and Negishi coupling reactions is described.

引用

页码：2154 / 2157

页数：4

共 21 条

[1] Switchable reactivity of acylated α,β-dehydroamino ester in the Friedel-Crafts alkylation of indoles by changing the Lewis acid [J].

Angelini, Elena ;

Balsamini, Cesarino ;

Bartoccini, Francesca ;

Lucarini, Simone ;

Piersanti, Giovanni .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14) :5654-5657

[2] Efficient preparation of 2-indolyl-1-nitroalkane derivatives employing nitroalkenes as versatile Michael acceptors:: New practical linear approach to alkyl 9H-β-Carboline-4-carboxylate [J].

Bartoli, G ;

Bosco, M ;

Giuli, S ;

Giuliani, A ;

Lucarelli, L ;

Marcantoni, E ;

Sambri, L ;

Torregiani, E .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (05) :1941-1944

[3] Chemistry of the hexahydropyrrolo[2,3-b]indoles:: Configuration, conformation, reactivity, and applications in synthesis [J].

Crich, David ;

Banerjee, Abhisek .

ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (02) :151-161

[4] Synthesis of enantiomerically pure β- and γ-amino acid derivatives using functionalized organozinc reagents [J].

Dexter, CS ;

Jackson, RFW ;

Elliott, J .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (20) :7579-7585

[5] An expeditious synthesis of C(3)-N(1′) heterodimeric indolines [J].

Espejo, Vinson R. ;

Rainier, Jon D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (39) :12894-+

[6] PALLADIUM-CATALYZED REACTIONS IN THE SYNTHESIS OF 3-SUBSTITUTED AND 4-SUBSTITUTED INDOLES - APPROACHES TO ERGOT ALKALOIDS [J].

HARRINGTON, PJ ;

HEGEDUS, LS .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (15) :2657-2662

[7] Concise synthesis of enantiomerically pure phenylalanine, homophenylalanine, and bishomophenylalanine derivatives using organozinc chemistry: NMR studies of amino acid-derived organozinc reagents [J].

Jackson, RFW ;

Moore, RJ ;

Dexter, CS ;

Elliot, J ;

Mowbray, CE .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7875-7884

[8]

MARIN J, 2004, EUR J ORG CHEM, V302, P7

[9] Amino-zinc-ene-enolate cyclization:: A short access to cis-3-substituted prolino-homotryptophane derivatives [J].

Mothes, Celine ;

Lavielle, Solange ;

Karoyan, Philippe .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17) :6706-6710

[10] More kapakahines from the marine sponge cribrochalina Olemda [J].

Nakao, Y ;

Kuo, J ;

Yoshida, WY ;

Kelly, M ;

Scheuer, PJ .

ORGANIC LETTERS, 2003, 5 (09) :1387-1390

← 1 2 3 →