Optically active allenes from β-lactone templates:: Asymmetric total synthesis of (-)-malyngolide

被引:101
作者
Wan, ZH [1 ]
Nelson, SG [1 ]
机构
[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
关键词
D O I
10.1021/ja002783u
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
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页码:10470 / 10471
页数:2
相关论文
共 40 条
[1]   MECHANISTIC ASPECTS ON THE FORMATION OF CHIRAL ALLENES FROM PROPARGYLIC ETHERS AND ORGANOCOPPER REAGENTS [J].
ALEXAKIS, A ;
MAREK, I ;
MANGENEY, P ;
NORMANT, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8042-8047
[2]   Organolanthanide-catalyzed hydroamination/cyclization. Efficient allene-based transformations for the syntheses of naturally occurring alkaloids [J].
Arredondo, VM ;
Tian, S ;
McDonald, FE ;
Marks, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (15) :3633-3639
[3]   A rapid synthesis of hydroxymethylacylfulvene (HMAF) using the allenic Pauson-Khand reaction. A synthetic approach to either enantiomer of this illudane structure [J].
Brummond, KM ;
Lu, JL ;
Petersen, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (20) :4915-4920
[4]  
BRUNEAU C, 1997, COMPREHENSIVE ORGANI, V1, P953
[5]   STRUCTURE AND ABSOLUTE-CONFIGURATION OF MALYNGOLIDE, AN ANTIBIOTIC FROM THE MARINE BLUE-GREEN-ALGA LYNGBYA-MAJUSCULA GOMONT [J].
CARDLLINA, JH ;
MOORE, RE ;
ARNOLD, EV ;
CLARDY, J .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (23) :4039-4042
[6]   ALLENES AND ACETYLENES .22. MECHANISTIC ASPECTS OF THE ALLENE-FORMING REDUCTIONS (SN2' REACTION) OF CHIRAL PROPARGYLIC DERIVATIVES WITH HYDRIDE REAGENTS [J].
CLAESSON, A ;
OLSSON, LI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (24) :7302-7311
[7]   SYNTHESIS OF THE 4 STEREOISOMERS OF ENPROSTIL [J].
COOPER, GF ;
WREN, DL ;
JACKSON, DY ;
BEARD, CC ;
GALEAZZI, E ;
VANHORN, AR ;
LI, TT .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) :4280-4286
[8]   SYNTHESIS AND STEREOCHEMISTRY OF ALLENES .3. HIGHLY STEREOSELECTIVE SYNTHESIS OF CHIRAL ALKYLALLENES BY ORGANOCOPPER(I)-INDUCED ANTI 1,3-SUBSTITUTION OF CHIRAL PROPYNYL ESTERS [J].
ELSEVIER, CJ ;
VERMEER, P .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (15) :3726-3730
[9]   Novel asymmetric syntheses of (-)-malyngolide and (+)-epi-malyngolide [J].
Enders, D ;
Knopp, M .
TETRAHEDRON, 1996, 52 (16) :5805-5818
[10]  
Florke H, 1996, LIEBIGS ANN, P147