Total Synthesis of (-)-Aspergilazine A

被引：23

作者：

Boyd, Emily M. ^{[1
]}

Sperry, Jonathan ^{[1
]}

机构：

[1] Univ Auckland, Sch Chem Sci, Auckland 1, New Zealand

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 19期

关键词：

CATALYZED N-ARYLATION; BOND FORMATION; (+)-NASESEAZINES; NITROGEN;

D O I：

10.1021/ol5024097

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of (-)-aspergilazine A, an alkaloid possessing a rare N1' to C6 bisindole bond, is described. A palladium-catalyzed N-arylation was used to selectively install the N1'-C6 bond in the presence of three other possible arylation sites. The ligand XPhos displayed a unique capability to efficiently carry out the N-arylation while simultaneously suppressing epimerization of the sensitive C9 stereocenters. This total synthesis has confirmed that aspergilazine A is a dimer of brevianamide F.

引用

页码：5056 / 5059

页数：4

共 33 条

[1] 4,7-Dimethoxy-1,10-phenanthroline:: An excellent ligand for the Cu-catalyzed N-arylation of imidazoles [J].

Altman, Ryan A. ;

Buchwald, Stephen L. .

ORGANIC LETTERS, 2006, 8 (13) :2779-2782

[2] Monodentate phosphines provide highly active catalysts for Pd-catalyzed C-N bond-forming reactions of heteroaromatic halides/amines and (H)N-heterocycles [J].

Anderson, Kevin W. ;

Tundel, Rachel E. ;

Ikawa, Takashi ;

Altman, Ryan A. ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) :6523-6527

[3] The copper-catalyzed N-arylation of indoles [J].

Antilla, JC ;

Klapars, A ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) :11684-11688

[4] STUDIES IN RELATION TO BIOSYNTHESIS .44. STRUCTURAL ELUCIDATIONS OF BREVIANAMIDE-B, BREVIANAMIDE-C, BREVIANAMIDE-D AND BREVIANAMIDE-F [J].

BIRCH, AJ ;

RUSSELL, RA .

TETRAHEDRON, 1972, 28 (11) :2999-&

[5] Total synthesis of putative montamine and a proposed structural reassignment [J].

Blair, Lachlan M. ;

Davie, Elizabeth A. Colby ;

Sperry, Jonathan .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (35) :6878-6884

[6] The facile synthesis of a series of tryptophan derivatives [J].

Blaser, Georg ;

Sanderson, John M. ;

Batsanov, Andrei S. ;

Howard, Judith A. K. .

TETRAHEDRON LETTERS, 2008, 49 (17) :2795-2798

[7] Synthetic studies towards dendridine A: synthesis of hemi-dendridine A acetate by Fischer indolization [J].

Boyd, Emily M. ;

Sperry, Jonathan .

TETRAHEDRON LETTERS, 2012, 53 (28) :3623-3626

[8] Brief total synthesis of the cell cycle inhibitor tryprostatin B and related preparation of its alanine analogue [J].

Caballero, E ;

Avendaño, C ;

Menéndez, JC .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :6944-6951

[9] Aspergilazine A, a diketopiperazine dimer with a Rare N-1 to C-6 linkage, from a marine-derived fungus Aspergillus taichungensis (vol 53, pg 2615, 2012) [J].

Cai, Shengxin ;

Kong, Xianglan ;

Wang, Wei ;

Zhou, Huinan ;

Zhu, Tianjiao ;

Li, Dehai ;

Gu, Qianqun .

TETRAHEDRON LETTERS, 2014, 55 (39) :5404-5404

[10] Aspergilazine A, a diketopiperazine dimer with a rare N-1 to C-6 linkage, from a marine-derived fungus Aspergillus taichungensis [J].