Towards the synthesis of amphidinolide B. An intramolecular Stille coupling approach

被引:34
作者
Cid, MB [1 ]
Pattenden, G [1 ]
机构
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
关键词
D O I
10.1016/S0040-4039(00)01242-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthetic approach towards the cytotoxic polyene polyol macrolide amphidinolide B (1), based on elaboration of the C-1-C-13 carboxylic acid 4 and the C-14-C-25 alcohol 3 units, their esterification to the iodostannyl ester 2, and an intramolecular Stille sp(2)-sp(2) coupling reaction, is described. In spite of adequate precedent and model experiments, circumstances conspired and the aforementioned coupling reaction was not realised in this case. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7373 / 7378
页数:6
相关论文
共 37 条
  • [1] Copper-mediated cross-coupling of organostannanes with organic iodides at or below room temperature
    Allred, GD
    Liebeskind, LS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (11) : 2748 - 2749
  • [2] A DIRECT SYNTHESIS OF OLEFINS BY REACTION OF CARBONYL-COMPOUNDS WITH LITHIO DERIVATIVES OF 2-[ALKYL-SULFONYL OR (2'-ALKENYL)-SULFONYL OR BENZYL-SULFONYL]-BENZOTHIAZOLES
    BAUDIN, JB
    HAREAU, G
    JULIA, SA
    RUEL, O
    [J]. TETRAHEDRON LETTERS, 1991, 32 (09) : 1175 - 1178
  • [3] THE STRUCTURES OF AMPHIDINOLIDE-B ISOMERS - STRONGLY CYTOTOXIC MACROLIDES PRODUCED BY A FREE-SWIMMING DINOFLAGELLATE, AMPHIDINIUM SP
    BAUER, I
    MARANDA, L
    SHIMIZU, Y
    PETERSON, RW
    CORNELL, L
    STEINER, JR
    CLARDY, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) : 2657 - 2658
  • [4] Bellingham R, 1996, SYNTHESIS-STUTTGART, P285
  • [5] Blakemore PR, 1998, SYNLETT, P26
  • [6] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS
    BLANCHETTE, MA
    CHOY, W
    DAVIS, JT
    ESSENFELD, AP
    MASAMUNE, S
    ROUSH, WR
    SAKAI, T
    [J]. TETRAHEDRON LETTERS, 1984, 25 (21) : 2183 - 2186
  • [7] Chakraborty TK, 1999, SYNLETT, P150
  • [8] Synthetic studies toward potent cytotoxic agent amphidinolide B: Synthesis of the entire C-1-C-13 moiety of the bottom half
    Chakraborty, TK
    Suresh, VR
    [J]. CHEMISTRY LETTERS, 1997, (06) : 565 - 566
  • [9] Synthetic studies toward potent cytotoxic agent amphidinolide B: Synthesis of the entire C14-C26 moiety of the top half
    Chakraborty, TK
    Thippeswamy, D
    Suresh, VR
    Jayaprakash, S
    [J]. CHEMISTRY LETTERS, 1997, (06) : 563 - 564
  • [10] CHAKRABORTY TK, 1999, CHEM LETT, P150