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
[1]  
Amans D., 2006, ANGEW CHEM, V118, P6002
[2]   Synthesis of a promising immunosuppressant: FR252921 [J].
Amans, Dominique ;
Bellosta, Veronique ;
Cossy, Janine .
ORGANIC LETTERS, 2007, 9 (23) :4761-4764
[3]   Total synthesis of pseudotrienic acid B:: A bioactive metabolite from Pseudomonas sp MF 381-IODS [J].
Amans, Dominique ;
Bellosta, Veronique ;
Cossy, Janine .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (35) :5870-5874
[4]   SYNTHESIS OF OPTICALLY-ACTIVE T-BUTYL (3R,5S)-3,5-ISOPROPYLIDENEDIOXY-6-HEPTYNOATE THROUGH BAKERS-YEAST REDUCTION OF METHYL 3-OXO-4-PENTYNOATE [J].
ANSARI, MH ;
KUSUMOTO, T ;
HIYAMA, T .
TETRAHEDRON LETTERS, 1993, 34 (51) :8271-8274
[5]  
Betzer JF, 1998, SYNLETT, P1129
[6]   Palladium-catalysed hydrostannylations of 1-bromoalkynes. A practical synthesis of (E)-1-stannylalk-1-enes [J].
Boden, CDJ ;
Pattenden, G ;
Ye, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (20) :2417-2419
[8]   A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].
CARLSEN, PHJ ;
KATSUKI, T ;
MARTIN, VS ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938
[9]   First total synthesis of (±)-taxifolial A and (±)-iso-caulerpenyne [J].
Commeiras, L ;
Santelli, M ;
Parrain, JL .
ORGANIC LETTERS, 2001, 3 (11) :1713-1715
[10]   A very short, efficient and inexpensive synthesis of the prodrug form of SC-54701A - A platelet aggregation inhibitor [J].
Cossy, J ;
Schmitt, A ;
Cinquin, C ;
Buisson, D ;
Belotti, D .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (13) :1699-1700