Stereoselective synthesis of the phorboxazole A macrolide by ring-closing metathesis

被引：22

作者：

Wang, Bo ^{[1
]}

Forsyth, Craig J. ^{[1
]}

机构：

[1] Univ Minnesota, Inst Technol, Dept Chem, Minneapolis, MN 55455 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 23期

关键词：

D O I：

10.1021/ol0619922

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Described is a regio- and stereoselective ring-closing metathesis (RCM) to form the C2-C3 alkene of the macrolide-containing domain of phorboxazole A. This work demonstrates a dramatic effect of reaction solvent on RCM product (E/Z)-selectivity. This process offers an alternative assembly of the macrolide-containing domain of phorboxazole A, one of the most potent anticancer agents known.

引用

页码：5223 / 5226

页数：4

共 50 条

[21] Synthesis of "glycospirostanes" via ring-closing metathesis [J].

Czajkowska, Dorota ;

Morzycki, Jacek W. ;

Santillan, Rosa ;

Siergiejczyk, Leszek .

STEROIDS, 2009, 74 (13-14) :1073-1079

[22] Ring-closing metathesis in the synthesis of fused sultones [J].

Mondal, Shovan ;

Debnath, Sudatshan .

TETRAHEDRON LETTERS, 2014, 55 (09) :1577-1580

[23] Synthesis of cyclic enehydrazides by ring-closing metathesis [J].

Lebrun, Stephane ;

Couture, Axel ;

Deniau, Eric ;

Grandclaudon, Pierre .

SYNTHESIS-STUTTGART, 2006, (20) :3490-3494

[24] Synthesis of cyclic dipeptides by ring-closing metathesis [J].

Reichwein, JF ;

Liskamp, RMJ .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 2000 (12) :2335-2344

[25] Synthesis of Berkeleylactone A by Ring-Closing Alkyne Metathesis [J].

Schmidt, Frank ;

Ammanath, Aparna Viswanathan ;

Goetz, Friedrich ;

Maier, Martin E. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (36)

[26] Synthesis of vinyl fluorides by ring-closing metathesis [J].

Marhold, M ;

Buer, A ;

Hiemstra, H ;

van Maarseveen, JH ;

Haufe, G .

TETRAHEDRON LETTERS, 2004, 45 (01) :57-60

[27] Synthesis of Macrocyclic β-Peptidomimetics by Ring-Closing Metathesis [J].

Dinh Hieu Tran ;

Xuan Tu Nguyen ;

Thi Minh Chau Tran ;

Thuy Quynh Le ;

Chang Ho Oh ;

Dinh Hung Mac .

CHEMISTRYSELECT, 2020, 5 (39) :12232-12235

[28] Synthesis of macrocyclic natural products by catalyst-controlled stereoselective ring-closing metathesis [J].

Miao Yu ;

Chenbo Wang ;

Andrew F. Kyle ;

Pavol Jakubec ;

Darren J. Dixon ;

Richard R. Schrock ;

Amir H. Hoveyda .

Nature, 2011, 479 :88-93

[29] Stereoselective synthesis of the naturally occurring lactones (-)-osmundalactone and (-)-muricatacine using ring-closing metathesis [J].

Carda, M ;

Rodríguez, S ;

González, F ;

Castillo, E ;

Villanueva, A ;

Marco, JA .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (15) :2649-2655

[30] Stereoselective approaches to the synthesis of marine polyethers using ring-closing metathesis reactions. [J].

Clark, JS ;

Kettle, JG ;

Hufton, R ;

Hamelin, O ;

Trevitt, G .

ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 :U518-U518

← 1 2 3 4 5 →