Total Synthesis of (±)-Communesin F via a Cycloaddition with Indol-2-one

被引：98

作者：

Belmar, Johannes ^{[1
]}

Funk, Raymond L. ^{[1
]}

机构：

[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 41期

基金：

美国国家卫生研究院;

关键词：

COMMUNESINS; PEROPHORAMIDINE; NOMOFUNGIN; ALKALOIDS;

D O I：

10.1021/ja307277w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise total synthesis of (+/-)-communesin F has been completed in 15 linear steps from 4-bromotryptophol in an overall yield of 6.7%. A key step features the cycloaddition of indol-2-one with 3-(2-azidoethyl)-4-bromoindole and facilitates the rapid construction of the lower aminal-containing tetracyclic core of the natural product.

引用

页码：16941 / 16943

页数：3

共 29 条

[11] A synthetic approach to the communesins [J].

George, Jonathan H. ;

Adlington, Robert M. .

SYNLETT, 2008, (14) :2093-2096

[12] New insecticidal compounds, communesins C, D and E, from Penicillium expansum link MK-57 [J].

Hayashi, H ;

Matsumoto, H ;

Akiyama, K .

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2004, 68 (03) :753-756

[13] REACTIONS OF 3-BROMOOXINDOLES - SYNTHESIS OF 3-METHYLENEOXINDOLE [J].

HINMAN, RL ;

BAUMAN, CP .

JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (08) :2431-&

[14] New communesin derivatives from the fungus Penicillium sp derived from the Mediterranean sponge Axinella verrucosa [J].

Jadulco, R ;

Edrada, RA ;

Ebel, R ;

Berg, A ;

Schaumann, K ;

Wray, V ;

Steube, K ;

Proksch, P .

JOURNAL OF NATURAL PRODUCTS, 2004, 67 (01) :78-81

[15] Enantioselective synthesis of (-)-cis-clavicipitic acid [J].

Ku, Jin-Mo ;

Jeong, Byeong-Seon ;

Jew, Sang-sup ;

Park, Hyeung-geun .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (21) :8115-8118

[16] Total Synthesis of the Polycyclic Fungal Metabolite (±)-Communesin F [J].

Liu, Peng ;

Seo, Jae Hong ;

Weinreb, Steven M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (11) :2000-2003

[17] Biomimetic approach to communesin B (a.k.a. nomofungin) [J].

May, JA ;

Zeidan, RK ;

Stoltz, BM .

TETRAHEDRON LETTERS, 2003, 44 (06) :1203-1205

[18] The structural and synthetic implications of the biosynthesis of the calycanthaceous alkaloids, the communesins, and nomofungin [J].

May, Jeremy A. ;

Stoltz, Brian .

TETRAHEDRON, 2006, 62 (22) :5262-5271

[19] COMMUNESINS, CYTOTOXIC METABOLITES OF A FUNGUS ISOLATED FROM A MARINE ALGA [J].

NUMATA, A ;

TAKAHASHI, C ;

ITO, Y ;

TAKADA, T ;

KAWAI, K ;

USAMI, Y ;

MATSUMURA, E ;

IMACHI, M ;

ITO, T ;

HASEGAWA, T .

TETRAHEDRON LETTERS, 1993, 34 (14) :2355-2358

[20] 2-Thioindoles as precursors to spiro-fused indolines:: Synthesis of (±)-dehaloperophoramidine [J].

Sabahi, Amir ;

Novikov, Alexei ;

Rainier, Jon D. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) :4317-4320

← 1 2 3 →