Total Synthesis of (±)-Streptonigrin: De Novo Construction of a Pentasubstituted Pyridine using Ring-Closing Metathesis

被引：50

作者：

Donohoe, Timothy J. ^{[1
]}

Jones, Christopher R. ^{[1
]}

Barbosa, Luiz C. A. ^{[2
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

[2] Univ Fed Vicosa, Dept Chem, BR-36570000 Vicosa, MG, Brazil

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 41期

关键词：

CROSS-COUPLING STRATEGIES; STREPTONIGRIN; LAVENDAMYCIN; DEGRADATION; DERIVATIVES; CONNECTION; METALATION; ANALOGS; AGENTS; DNA;

D O I：

10.1021/ja207835w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of the potent antitumor agent (+/-)-streptonigrin has been achieved in 14 linear steps and 11% overall yield from ethyl glyoxalate. The synthesis features a challenging ring-closing metathesis reaction, followed by elimination and aromatization, to furnish a key pentasubstituted pyridine fragment.

引用

页码：16418 / 16421

页数：4

共 50 条

[31] Ring-closing metathesis for the synthesis of a molecular gyrotop
Setaka, Wataru
Higa, Sayaka
Yamaguchi, Kentaro
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (21) : 3354 - 3357
[32] Synthesis of cyclic sulfones by ring-closing metathesis
Yao, QW
ORGANIC LETTERS, 2002, 4 (03) : 427 - 430
[33] A ring-closing metathesis approach for the synthesis of (±)-pregabalin
Bobade, Vivek D.
Mhaske, Pravin C.
Vadgaonkar, Kamlesh S.
Shelke, Shivaji H.
MONATSHEFTE FUR CHEMIE, 2012, 143 (05): : 847 - 851
[34] Synthesis of cyclitols via ring-closing metathesis
Kornienko, A
d'Alarcao, M
TETRAHEDRON-ASYMMETRY, 1999, 10 (05) : 827 - 829
[35] Synthesis of "glycospirostanes" via ring-closing metathesis
Czajkowska, Dorota
Morzycki, Jacek W.
Santillan, Rosa
Siergiejczyk, Leszek
STEROIDS, 2009, 74 (13-14) : 1073 - 1079
[36] Ring-closing metathesis as a basis for the construction of aromatic compounds
Donohoe, TJ
Orr, AJ
Bingham, M
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (17) : 2664 - 2670
[37] Synthesis of cyclic enehydrazides by ring-closing metathesis
Lebrun, Stephane
Couture, Axel
Deniau, Eric
Grandclaudon, Pierre
SYNTHESIS-STUTTGART, 2006, (20): : 3490 - 3494
[38] Ring-closing metathesis in the synthesis of fused sultones
Mondal, Shovan
Debnath, Sudatshan
TETRAHEDRON LETTERS, 2014, 55 (09) : 1577 - 1580
[39] Synthesis of cyclic dipeptides by ring-closing metathesis
Reichwein, JF
Liskamp, RMJ
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 2000 (12) : 2335 - 2344
[40] Dienyne ring-closing metathesis approach for the construction of taxosteroids
Aldegunde, Maria J.
Garcia-Fandino, Rebeca
Castedo, Luis
Granja, Juan R.
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (18) : 5135 - 5150

← 1 2 3 4 5 →