Total synthesis of pseudotrienic acid B:: A bioactive metabolite from Pseudomonas sp MF 381-IODS

被引:12
作者
Amans, Dominique [1 ]
Bellosta, Veronique [1 ]
Cossy, Janine [1 ]
机构
[1] ESPCI, Associe CNRS, Chim Organ Lab, F-75231 Paris 05, France
关键词
cross-coupling; crotyltitanation; metathesis; natural products; total synthesis;
D O I
10.1002/anie.200601114
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Acid advancement: An efficient and highly convergent stereoselective synthesis of pseudotrienic acid B (see structure) has been achieved. Synthetic highlights include a crotyltitanation reaction to control the stereogenic centers at C11 and C20, a cross-metathesis reaction to synthesize the triene moiety, and a Stille cross-coupling reaction to complete the assembly of the carbon framework of the natural product. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:5870 / 5874
页数:5
相关论文
共 23 条
[1]   REGIOCONTROLLED AND STEREOCONTROLLED STANNYLMETALLATION OF 3,3-DIETHOXY-PROP-1-YNE AND 4,4-DIETHOXY-BUT-1-YNE - AN EFFICIENT ACCESS TO THE CORRESPONDING VINYLTINS WITH FIXED CONFIGURATIONS [J].
BEAUDET, I ;
PARRAIN, JL ;
QUINTARD, JP .
TETRAHEDRON LETTERS, 1991, 32 (44) :6333-6336
[2]   Radical hydrostannylation, Pd(0)-catalyzed hydrostannylation, stannylcupration of propargyl alcohols and enynols: Regio- and stereoselectivities [J].
Betzer, JF ;
Delaloge, F ;
Muller, B ;
Pancrazi, A ;
Prunet, J .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7768-7780
[3]  
BETZER JF, 1988, SYNTHESIS-STUTTGART, P522
[4]   First total synthesis of (±)-taxifolial A and (±)-iso-caulerpenyne [J].
Commeiras, L ;
Santelli, M ;
Parrain, JL .
ORGANIC LETTERS, 2001, 3 (11) :1713-1715
[5]   Assembling heterocycle-tethered C-glycosyl and α-amino acid residues via 1,3-dipolar cycloaddition reactions [J].
Dondoni, A ;
Giovannini, PP ;
Massi, A .
ORGANIC LETTERS, 2004, 6 (17) :2929-2932
[6]   FR252921, a novel immunosuppressive agent isolated from Pseudomonas fluorescens No. 408813 -: I.: Taxonomy, fermentation, isolation, physico-chemical properties and biological activities of FR252921, FR252922 and FR256523 [J].
Fujine, K ;
Tanaka, M ;
Ohsumi, K ;
Hashimoto, M ;
Takase, S ;
Ueda, H ;
Hino, M ;
Fujii, T .
JOURNAL OF ANTIBIOTICS, 2003, 56 (02) :55-61
[7]   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
[8]   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
[9]   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
[10]   A recyclable Ru-based metathesis catalyst [J].
Kingsbury, JS ;
Harrity, JPA ;
Bonitatebus, PJ ;
Hoveyda, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (04) :791-799