Stereocontrolled synthesis of (+)-boronolide

被引:86
作者
Trost, BM [1 ]
Yeh, VSC [1 ]
机构
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
关键词
D O I
10.1021/ol026665i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Boronolide was synthesized stereoselectively from hydroxyacetylfuran 5 and valeraldehyde 6 using a novel dizinc aldol catalyst. Ring closing metathesis provides the lactone ring. The synthesis requires 12 steps and proceeds in 26% overall yield.
引用
收藏
页码:3513 / 3516
页数:4
相关论文
共 44 条
  • [1] [Anonymous], 2000, Catalytic asymmetric synthesis
  • [2] [Anonymous], CATALYTIC ASYMMETRIC
  • [3] Armstrong SK, 1998, J CHEM SOC PERK T 1, P371
  • [4] CHIRAL SYNTHESIS VIA ORGANOBORANES .21. ALLYLBORATION AND CROTYLBORATION OF ALPHA-CHIRAL ALDEHYDES WITH DIISOPINOCAMPHEYLBORON AS THE CHIRAL AUXILIARY
    BROWN, HC
    BHAT, KS
    RANDAD, RS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) : 1570 - 1576
  • [5] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS
    CARLSEN, PHJ
    KATSUKI, T
    MARTIN, VS
    SHARPLESS, KB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) : 3936 - 3938
  • [6] CARREIRA EM, 1999, COMPREHENSIVE ASYMME, V3, P998
  • [7] STEREOCHEMICAL STUDIES ON BORONOLIDE, AN ALPHA-PYRONE FROM TETRADENIA-BARBERAE
    DAVIESCOLEMAN, MT
    RIVETT, DEA
    [J]. PHYTOCHEMISTRY, 1987, 26 (11) : 3047 - 3050
  • [8] Applications of sugar nitrones in synthesis: The total synthesis of (+)-polyoxin J
    Dondoni, A
    Franco, S
    Junquera, F
    Merchan, FL
    Merino, P
    Tejero, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) : 5497 - 5507
  • [9] Enders D, 2002, SYNLETT, P962
  • [10] EVANS DA, 1984, ASYMMETRIC SYNTHES B, V3, P2