Synthesis of Two Bioactive Natural Products: FR252921 and Pseudotrienic Acid B

被引:31
作者
Amans, Dominique [1 ]
Bellosta, Veronique [1 ]
Cossy, Janine [1 ]
机构
[1] ESPCI ParisTcch, CNRS, Chim Organ Lab, F-75231 Paris 05, France
关键词
asymmetric catalysis; cross-coupling; metathesis; natural products; polyenes; TITANIUM-CARBOHYDRATE COMPLEXES; FLUORESCENS NO. 408813; ENANTIOSELECTIVE SYNTHESES; SELECTIVE SYNTHESIS; MIXED ANHYDRIDE; ALDOL-REACTION; EFFICIENT; CONSTRUCTION; ALKYNES; MACROLACTONIZATION;
D O I
10.1002/chem.200802649
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Concise and highly convergent syntheses of the immunosuppressive agent FR252921 and the related antimicrobial natural product pseudotrienic acid B were achieved from a common intermediate by using optically active titanium complexes to control the configuration of the stereogenic centers, a highly stereo and regioselective cross-metathesis to generate the triene moieties, and a Stille cross-coupling to install the dienic units.
引用
收藏
页码:3457 / 3473
页数:17
相关论文
共 49 条
[21]   FR252921, a novel immunosuppressive agent isolated from Pseudomonas fluorescens No. 408813 -: II.: In vitro property and mode of action [J].
Fujine, K ;
Abe, F ;
Seki, N ;
Ueda, H ;
Hino, M ;
Fujii, T .
JOURNAL OF ANTIBIOTICS, 2003, 56 (02) :62-67
[22]   FR252921, a novel immunosuppressive agent isolated from Pseudomona fluorescens No. 408813 -: III.: In vivo activities [J].
Fujine, K ;
Ueda, H ;
Hino, M ;
Fujii, T .
JOURNAL OF ANTIBIOTICS, 2003, 56 (02) :68-71
[23]  
Furstner A., 2006, ANGEW CHEM, V118, P5964
[24]   Efficient and recyclable monomeric and dendritic Ru-based metathesis catalysts [J].
Garber, SB ;
Kingsbury, JS ;
Gray, BL ;
Hoveyda, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) :8168-8179
[25]   ENANTIOSELECTIVE ALLYLTITANATION OF ALDEHYDES WITH CYCLOPENTADIENYLDIALKOXYALLYLTITANIUM COMPLEXES [J].
HAFNER, A ;
DUTHALER, RO ;
MARTI, R ;
RIHS, G ;
ROTHESTREIT, P ;
SCHWARZENBACH, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (07) :2321-2336
[26]   A convenient and genuine equivalent to HZrCp2Cl generated in situ from ZrCp2Cl2-DIBAL-H [J].
Huang, Zhihong ;
Negishi, Ei-ichi .
ORGANIC LETTERS, 2006, 8 (17) :3675-3678
[27]   RAPID ESTERIFICATION BY MEANS OF MIXED ANHYDRIDE AND ITS APPLICATION TO LARGE-RING LACTONIZATION [J].
INANAGA, J ;
HIRATA, K ;
SAEKI, H ;
KATSUKI, T ;
YAMAGUCHI, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (07) :1989-1993
[28]   MODEL STUDIES FOR THE SYNTHESIS OF QUASSINOIDS .1. CONSTRUCTION OF THE BCE RING-SYSTEM [J].
KRAUS, GA ;
TASCHNER, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (06) :1175-1176
[29]   TRANSMETALATION REACTIONS OF HIGHER-ORDER CYANOCUPRATES - DIRECT FORMATION OF TRIALKYLTIN CUPRATES FROM TIN HYDRIDES WHICH BYPASSES ORGANO-LITHIUM INTERMEDIATES [J].
LIPSHUTZ, BH ;
ELLSWORTH, EL ;
DIMOCK, SH ;
REUTER, DC .
TETRAHEDRON LETTERS, 1989, 30 (16) :2065-2068
[30]   Efficient and stereoselective synthesis of freelingyne via Pd-catalyzed cross coupling and lactonization [J].
Liu, F ;
Negishi, E .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (24) :8591-8594