Total synthesis of reblastatin

被引：59

作者：

Wrona, IE

Gabarda, AE

Evano, G

Panek, JS

机构：

[1] Boston Univ, Metcalf Ctr Sci & Engn, Dept Chem, Boston, MA 02215 USA

[2] Boston Univ, Metcalf Ctr Sci & Engn, Ctr Chem Methodol & Lib Dev, Boston, MA 02215 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 43期

关键词：

D O I：

10.1021/ja055384d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantioselective total synthesis of reblastatin is described. The synthesis highlights hydrozirconation, transmetalation, aldehyde addition sequence to install E-trisubstituted olefin and C7 stereocenter, and the first use of an intramolecular Buchwald-like amidation reaction to close the 19-membered macrolactam. Copyright © 2005 American Chemical Society.

引用

收藏

页码：15026 / 15027

页数：2

相关论文

共 27 条

[1] A convenient synthesis of dimethyl (diazomethyl)phosphonate (Seyferth Gilbert reagent) [J].

Brown, DG ;

Velthuisen, EJ ;

Commerford, JR ;

Brisbois, RG ;

Hoye, TR .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) :2540-2541

[2]

CONGREVE MS, 1993, SYNLETT, P663

[3] GELDANAMYCIN, A NEW ANTIBIOTIC [J].

DEBOER, C ;

MEULMAN, PA ;

WNUK, RJ ;

PETERSON, DH .

JOURNAL OF ANTIBIOTICS, 1970, 23 (09) :442-&

[4] DIAZOETHENES - THEIR ATTEMPTED SYNTHESIS FROM ALDEHYDES AND AROMATIC KETONES BY WAY OF THE HORNER-EMMONS MODIFICATION OF THE WITTIG REACTION - A FACILE SYNTHESIS OF ALKYNES [J].

GILBERT, JC ;

WEERASOORIYA, U .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (10) :1837-1845

[5] Total synthesis of thyrsiferyl 23-acetate, a specific inhibitor of protein phosphatase 2A and an anti-leukemic inducer of apoptosis [J].

González, IC ;

Forsyth, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (38) :9099-9108

[6]

HERDEIS C, 1986, SYNTHESIS-STUTTGART, P232

[7] Enantioselective synthesis of the protein phosphatase inhibitor (-)-motuporin [J].

Hu, T ;

Panek, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (38) :11368-11378

[8] A general and efficient copper catalyst for the amidation of aryl halides [J].

Klapars, A ;

Huang, XH ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (25) :7421-7428

[9] CARBAMATES - A METHOD OF SYNTHESIS AND SOME SYNTHETIC APPLICATIONS [J].

KOCOVSKY, P .

TETRAHEDRON LETTERS, 1986, 27 (45) :5521-5524

[10] Synthesis of 1-aryl-1H-indazoles via palladium-catalyzed intramolecular amination of aryl halides [J].

Lebedev, AY ;

Khartulyari, AS ;

Voskoboynikov, AZ .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) :596-602