Synthesis of the pyrrolidinone core of KSM-2690 B

被引:45
作者
Donohoe, Timothy J. [1 ]
Chiu, Jessica Y. K. [1 ]
Thomas, Rhian E. [1 ]
机构
[1] Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England
关键词
D O I
10.1021/ol062705x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first synthesis of the pyrrolidinone core of the polyene beta-lactone antibiotic KSM-2690 B is described. An ammonia-free Birch reductive aldol reaction utilizing acetaldehyde is one of the key steps, together with a ruthenium-catalyzed alkene isomerization reaction.
引用
收藏
页码:421 / 424
页数:4
相关论文
共 32 条
[1]   STEREOSPECIFIC INTRODUCTION OF DOUBLE-BONDS VIA THERMOLYSIS OF BETA-LACTONES [J].
ADAM, W ;
BAEZA, J ;
LIU, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (06) :2000-&
[2]  
Andrews MD, 1996, SYNLETT, P612
[3]   Development of isomerization and cycloisomerization with use of a ruthenium hydride with N-heterocyclic carbene and its application to the synthesis of heterocycles [J].
Arisawa, Mitsuhiro ;
Terada, Yukiyoshi ;
Takahashi, Kazuyuki ;
Nakagawa, Masako ;
Nishida, Atsushi .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (11) :4255-4261
[4]   OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES [J].
BAL, BS ;
CHILDERS, WE ;
PINNICK, HW .
TETRAHEDRON, 1981, 37 (11) :2091-2096
[5]   A multicomponent coupling strategy suitable for the synthesis of the triene component of the oxazolomycin antibiotics [J].
Bulger, PG ;
Moloney, MG ;
Trippier, PC .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (21) :3726-3737
[6]  
Bulger PG, 2002, SYNLETT, P1871
[7]   Efficient synthesis of (S)-3,4-dihydro-2-pivaloyloxymethyl-2H-pyrrole 1-oxide [J].
Busqué, F ;
de March, P ;
Figueredo, M ;
Font, J ;
Gallagher, T ;
Milán, S .
TETRAHEDRON-ASYMMETRY, 2002, 13 (04) :437-445
[8]   A versatile and highly selective hypervalent iodine (III)/2,2,6,6-tetramethyl-1-piperidinyloxyl-mediated oxidation of alcohols to carbonyl compounds [J].
DeMico, A ;
Margarita, R ;
Parlanti, L ;
Vescovi, A ;
Piancatelli, G .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :6974-6977
[9]   Utility of the ammonia-free birch reduction of electron-deficient pyrroles:: Total synthesis of the 20S proteasome inhibitor, clasto-lactacystin β-lactone [J].
Donohoe, TJ ;
Sintim, HO ;
Sisangia, L ;
Ace, KW ;
Guyo, PM ;
Cowley, A ;
Harling, JD .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (14) :4227-4238
[10]   An efficient synthesis of lactacystin β-lactone [J].
Donohoe, TJ ;
Sintim, H ;
Sisangia, L ;
Harling, JD .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (17) :2293-2296