Synthesis (and alternative proof of configuration) of the scyphostatin C(1′)-C(20′) trienoyl fragment

被引:60
作者
Hoye, TR [1 ]
Tennakoon, MA [1 ]
机构
[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA
关键词
D O I
10.1021/ol0058386
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Each of four diastereomers of structure 2, corresponding to the lipophilic side chain of scyphostatin (1), were prepared. Careful analysis of their NMR spectral data and comparison with those of the natural product corroborates the recently reported (Org. Lett. 2000, 2, 505) stereochemical assignment. A strategy for the stereoselective synthesis of 2 has been achieved.
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页码:1481 / 1483
页数:3
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共 30 条
  • [21] The complete structure of maitotoxin .2. Configuration of the C135-C142 side chain and absolute configuration of the entire molecule
    Nonomura, T
    Sasaki, M
    Matsumori, N
    Murata, M
    Tachibana, K
    Yasumoto, T
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (15): : 1675 - 1678
  • [22] ABSOLUTE-CONFIGURATION OF C(1)-C(5) FRAGMENT OF AAL-TOXIN - CONFORMATIONALLY RIGID ACYCLIC AMINOTRIOL MOIETY
    OIKAWA, H
    MATSUDA, I
    ICHIHARA, A
    KOHMOTO, K
    [J]. TETRAHEDRON LETTERS, 1994, 35 (08) : 1223 - 1226
  • [23] OKUKADO N, 1978, TETRAHEDRON LETT, V19, P2357
  • [24] Absolute configuration of scyphostatin
    Saito, S
    Tanaka, N
    Fujimoto, K
    Kogen, H
    [J]. ORGANIC LETTERS, 2000, 2 (04) : 505 - 506
  • [25] The complete structure of maitotoxin .1. Configuration of the C1-C14 side chain
    Sasaki, M
    Matsumori, N
    Maruyama, T
    Nonomura, T
    Murata, M
    Tachibana, K
    Yasumoto, T
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (15): : 1672 - &
  • [26] Structural elucidation of scyphostatin, an inhibitor of membrane-bound neutral sphingomyelinase
    Tanaka, M
    Nara, F
    SuzukiKonagai, K
    Hosoya, T
    Ogita, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (33) : 7871 - 7872
  • [27] Macquarimicin A inhibits membrane-bound neutral sphingomyelinase from rat brain
    Tanaka, M
    Nara, F
    Yamasato, Y
    Masuda-Inoue, S
    Doi-Yoshioka, H
    Kumakura, S
    Enokita, R
    Ogita, T
    [J]. JOURNAL OF ANTIBIOTICS, 1999, 52 (07) : 670 - 673
  • [28] F-11334s, new inhibitors of membrane-bound neutral sphingomyelinase
    Tanaka, M
    Nara, F
    Yamasato, Y
    Ono, Y
    Ogita, T
    [J]. JOURNAL OF ANTIBIOTICS, 1999, 52 (09) : 827 - 830
  • [29] ERYTHROMYCIN .10. STRUCTURE OF ERYTHROMYCIN
    WILEY, PF
    GERZON, K
    FLYNN, EH
    SIGAL, MV
    WEAVER, O
    QUARCK, UC
    CHAUVETTE, RR
    MONAHAN, R
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (22) : 6062 - 6070
  • [30] Complete relative stereochemistry of maitotoxin
    Zheng, WJ
    DeMattei, JA
    Wu, JP
    Duan, JJW
    Cook, LR
    Oinuma, H
    Kishi, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (34) : 7946 - 7968