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

页码：15026 / 15027

页数：2

共 27 条

[1] A convenient synthesis of dimethyl (diazomethyl)phosphonate (Seyferth Gilbert reagent)
Brown, DG
Velthuisen, EJ
Commerford, JR
Brisbois, RG
Hoye, TR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) : 2540 - 2541
[2] CONGREVE MS, 1993, SYNLETT, P663
[3] GELDANAMYCIN, A NEW ANTIBIOTIC
DEBOER, C
MEULMAN, PA
WNUK, RJ
PETERSON, DH
[J]. 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
GILBERT, JC
WEERASOORIYA, U
[J]. 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
González, IC
Forsyth, CJ
[J]. 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
Hu, T
Panek, JS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (38) : 11368 - 11378
[8] A general and efficient copper catalyst for the amidation of aryl halides
Klapars, A
Huang, XH
Buchwald, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (25) : 7421 - 7428
[9] CARBAMATES - A METHOD OF SYNTHESIS AND SOME SYNTHETIC APPLICATIONS
KOCOVSKY, P
[J]. TETRAHEDRON LETTERS, 1986, 27 (45) : 5521 - 5524
[10] Synthesis of 1-aryl-1H-indazoles via palladium-catalyzed intramolecular amination of aryl halides
Lebedev, AY
Khartulyari, AS
Voskoboynikov, AZ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) : 596 - 602

← 1 2 3 →