Total synthesis of the salicylate enamide macrolide oximidine II

被引：104

作者：

Wang, X

Porco, JA

机构：

[1] Boston Univ, Dept Chem, Boston, MA 02215 USA

[2] Boston Univ, Ctr Chem Methodol, Boston, MA 02215 USA

[3] Boston Univ, Lib Dev, Boston, MA 02215 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 20期

关键词：

D O I：

10.1021/ja034030o

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The asymmetric synthesis of the salicylate enamide macrolide oximidine II is reported. The synthesis involves a highly regio- and stereoselective ring-closing metathesis of a bis-diene substrate to construct the macrocyclic triene core. Copper(I)-mediated amidation of a (Z)-vinyl iodide was employed to attach the enamide side chain. Copyright © 2003 American Chemical Society.

引用

页码：6040 / 6041

页数：2

共 32 条

[21] Approaches to oximidines, lobatamides and related natural products:: the coupling reactions of 3-iodoacrolein O-methyl oximes
Raw, SA
Taylor, RJK
[J]. TETRAHEDRON LETTERS, 2000, 41 (52) : 10357 - 10361
[22] Scheufler F, 2001, SYNLETT, P1221
[23] Total synthesis and stereochemical assignment of the salicylate antitumor macrolide lobatamide C
Shen, RC
Lin, CT
Porco, JA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (20) : 5650 - 5651
[24] Synthesis and V-ATPase inhibition of simplified lobatamide analogues
Shen, RC
Lin, CT
Bowman, EJ
Bowman, BJ
Porco, JA
[J]. ORGANIC LETTERS, 2002, 4 (18) : 3103 - 3106
[25] Synthesis of enamides related to the salicylate antitumor macrolides using copper-mediated vinylic substitution
Shen, RC
Porco, JA
[J]. ORGANIC LETTERS, 2000, 2 (09) : 1333 - 1336
[26] A STEREOSELECTIVE SYNTHESIS OF (Z)-1-IODO-1-ALKENES
STORK, G
ZHAO, K
[J]. TETRAHEDRON LETTERS, 1989, 30 (17) : 2173 - 2174
[27] The development of L2X2Ru=CHR olefin metathesis catalysts:: An organometallic success story
Trnka, TM
Grubbs, RH
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (01) : 18 - 29
[28] DIRECT, STEREOSELECTIVE SYNTHESIS OF EITHER E-1,3-DIENNES OR Z-1,3-DIENES
UKAI, J
IKEDA, Y
IKEDA, N
YAMAMOTO, H
[J]. TETRAHEDRON LETTERS, 1983, 24 (37) : 4029 - 4032
[29] Synthesis of macrolide analogues of sanglifehrin by RCM: Unique reactivity of a ruthenium carbene complex bearing an imidazol-2-ylidene ligand
Wagner, J
Cabrejas, LMM
Grossmith, CE
Papageorgiou, C
Senia, F
Wagner, D
France, J
Nolan, SP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) : 9255 - 9260
[30] MACROEXPANSION METHODOLOGY - MEDIUM RING SYNTHESIS BASED ON AN 8 UNIT RING EXPANSION PROCESS
WENDER, PA
SIEBURTH, SM
PETRAITIS, JJ
SINGH, SK
[J]. TETRAHEDRON, 1981, 37 (23) : 3967 - 3975

← 1 2 3 4 →