The enantioselective total synthesis and unambiguous proof of the absolute stereochemistry of pervilleine C

被引：13
|
作者：
Kulkarni, Ketav [1 ]
Zhao, Anne Y. [2 ]
Purcell, Anthony W. [2 ]
Perlmutter, Patrick [1 ]
机构：
[1] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia
[2] Univ Melbourne, Dept Biochem & Mol Biol, Bio Mol Sci & Biotechnol Inst 21, Melbourne, Vic 3010, Australia
来源：
SYNLETT | 2008年 / 14期
关键词：
pervilleines; MDR reversal; total synthesis; 4+3] cycloadditions; enantioselective oxidative hydroboration;
D O I：
10.1055/s-2008-1078255
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first enantioselective, total synthesis of the naturally occurring, potent cancer MDR reversal agent pervilleine C is reported. Each enantiomer of the natural product has been prepared as well as the enantiomers of the corresponding 8-oxa-pervilleine C.
引用
收藏
页码：2209 / 2212
页数：4
相关论文
共 50 条
  • [1] An enantioselective total synthesis of the stilbenolignan (-)-aiphanol and the determination of its absolute stereochemistry
    Banwell, MG
    Chand, S
    Savage, GP
    TETRAHEDRON-ASYMMETRY, 2005, 16 (09) : 1645 - 1654
  • [2] Enantioselective Total Synthesis and Confirmation of the Absolute and Relative Stereochemistry of Streptorubin B
    Hu, Dennis X.
    Clift, Michael D.
    Lazarski, Kiel E.
    Thomson, Regan J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (06) : 1799 - 1804
  • [3] Determination of relative and absolute stereochemistry of cephalosporolide D and its enantioselective total synthesis
    Shiina, I
    Fukuda, Y
    Ishii, T
    Fujisawa, H
    Mukaiyama, T
    CHEMISTRY LETTERS, 1998, (08) : 831 - 832
  • [4] Enantioselective synthesis for the antipodes of slagenins B and C: Establishment of absolute stereochemistry
    Jiang, B
    Liu, JF
    Zhao, SY
    ORGANIC LETTERS, 2001, 3 (25) : 4011 - 4013
  • [5] A rapid total synthesis of spirotryprostatin B: Proof of its relative and absolute stereochemistry
    von Nussbaum, F
    Danishefsky, SJ
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (12) : 2175 - +
  • [6] Enantioselective synthesis of phosphonothrixin and its absolute stereochemistry
    Tetrahedron Lett, 3 (437):
  • [7] Enantioselective synthesis of phosphonothrixin and its absolute stereochemistry
    Nakamura, K
    Yamamura, S
    TETRAHEDRON LETTERS, 1997, 38 (03) : 437 - 438
  • [8] Total synthesis of quinoxapeptin A-C: Establishment of absolute stereochemistry
    Boger, DL
    Ledeboer, MW
    Kume, M
    Jin, Q
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (16) : 2424 - 2426
  • [9] Total Synthesis and Absolute Stereochemistry of Seragakinone A
    Takada, Akiomi
    Hashimoto, Yoshimitsu
    Takikawa, Hiroshi
    Hikita, Katsuyoshi
    Suzuki, Keisuke
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (10) : 2297 - 2301
  • [10] The first enantioselective total synthesis of cyclomyltaylane-5α-ol and determination of its absolute stereochemistry
    Hagiwara, H
    Sakai, H
    Uchiyama, T
    Ito, Y
    Morita, N
    Hoshi, T
    Suzuki, T
    Ando, M
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (05): : 583 - 591
12345