Synthesis of the putative structure of fistulosin using the ruthenium-catalyzed cycloisomerization of diene

被引：35

作者：

Terada, Y ^{[1
]}

Arisawa, M ^{[1
]}

Nishida, A ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 03期

关键词：

D O I：

10.1021/jo0522005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fistulosin 1, which was isolated from the root of the Welsh onion, is a novel indole alkaloid that has antifungal activity. The first total synthesis of the reported structure of fistulosin using our cycloisomerization of diene is described. © 2006 American Chemical Society.

引用

页码：1269 / 1272

页数：4

共 31 条

[1] Development of novel reactions using ruthenium carbene catalyst and its application to novel methods for preparing nitrogen-containing heterocycles [J].

Arisawa, M ;

Terada, Y ;

Theeraladanon, C ;

Takahashi, K ;

Nakagawa, M ;

Nishida, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (24-25) :5398-5406

[2] Selective isomerization of a terminal olefin catalyzed by a ruthenium complex: The synthesis of indoles through ring-closing metathesis [J].

Arisawa, M ;

Terada, Y ;

Nakagawa, M ;

Nishida, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (24) :4732-4734

[3] Stereoselectivity in ring-closing olefin metathesis (RCM) of tethered dihexenoyl derivatives [J].

Arisawa, M ;

Kaneko, H ;

Nishida, A ;

Nakagawa, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (07) :959-964

[4]

Arisawa M, 1997, SYNLETT, P1179

[5]

Arisawa M, 2000, CHEM PHARM BULL, V48, P1593

[6] Concise synthesis of azacycloundecenes using ring-closing metathesis (RCM) [J].

Arisawa, M ;

Kato, C ;

Kaneko, H ;

Nishida, A ;

Nakagawa, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (12) :1873-1876

[7] The behavior of 1,n-enynes in the presence of transition metals [J].

Aubert, C ;

Buisine, O ;

Malacria, M .

CHEMICAL REVIEWS, 2002, 102 (03) :813-834

[8] TAUTOMERISM OF THE MONOHYDROXY DERIVATIVES OF 5-MEMBERED O, N, AND S HETEROCYCLES [J].

CAPON, B ;

KWOK, FC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) :5346-5356

[9] Recent developments in olefin cross-metathesis [J].

Connon, SJ ;

Blechert, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (17) :1900-1923

[10] Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis [J].

Deiters, A ;

Martin, SF .

CHEMICAL REVIEWS, 2004, 104 (05) :2199-2238

← 1 2 3 4 →