Total synthesis of (-)-callystatin A

被引：61
|
作者：
Langille, NF
Panek, JS
机构：
[1] Boston Univ, Dept Chem, Boston, MA 02215 USA
[2] Boston Univ, Ctr Chem Methodol & Library Dev, Metcalf Ctr Sci & Engn, Boston, MA 02215 USA
来源：
ORGANIC LETTERS | 2004年 / 6卷 / 18期
关键词：
D O I：
10.1021/ol048664r
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convergent enantioselective synthesis of the natural product (-)-callystatin A (1) is described. Key features of the synthesis include a lipase-mediated kinetic resolution to install the C5 lactone stereochemistry, a hydrozirconation-based approach to the C8-C9 trisubstituted (Z)-olefin, and a stereoselective cross-coupling of a vinyl dibromide to install the C14-C15 trisubstituted (E)-olefin.
引用
收藏
页码：3203 / 3206
页数：4
相关论文
共 50 条
  • [31] An iterative Shimizu non-aldol approach for the stereoselective synthesis of C13-C22 fragment of callystatin A
    Pujari, Sandip A.
    Kaliappan, Krishna P.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (09) : 1750 - 1753
  • [32] Synthesis of stereopentad analogues of the C14-C22 segment of callystatin A through additions of chiral allenylzinc reagents to stereotriads
    Marshall, JA
    Schaaf, GM
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23): : 7825 - 7831
  • [33] Synthesis of C13-C22 fragment of the marine sponge polyketide callystatin A (vol 43, pg 185, 2002)
    Dias, LC
    Meira, PRR
    TETRAHEDRON LETTERS, 2002, 43 (08) : 1593 - 1593
  • [34] Participation of the β-hydroxyketone part for potent cytotoxicity of callystatin A, a spongean polyketide
    Murakami, N
    Sugimoto, M
    Kobayashi, M
    BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (01) : 57 - 67
  • [35] Leptostatin: A synthetic hybrid of the cytotoxic polyketides callystatin A and leptomycin B
    Marshall, JA
    Mikowski, AM
    Bourbeau, MP
    Schaaf, GM
    Valeriote, F
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (02) : 320 - 323
  • [36] Convergency and divergency as strategic elements in total synthesis:: The total synthesis of (-)-drupacine and the formal total synthesis of (±)-Cephalotaxine, (-)-cephalotaxine, and (+)-cephalotaxine
    Liu, Qi
    Ferreira, Eric M.
    Stoltz, Brian M.
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (19): : 7352 - 7358
  • [37] Participation of the conjugated diene part for potent cytotoxicity of callystatin A, a spongean polyketide
    Murakami, N
    Sugimoto, M
    Nakajima, T
    Kawanishi, M
    Tsutsui, Y
    Kobayashi, M
    BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (11) : 2651 - 2661
  • [38] ASYMMETRIC TOTAL SYNTHESIS OF ERYTHROMYCIN .3. TOTAL SYNTHESIS OF ERYTHROMYCIN
    WOODWARD, RB
    LOGUSCH, E
    NAMBIAR, KP
    SAKAN, K
    WARD, DE
    AUYEUNG, BW
    BALARAM, P
    BROWNE, LJ
    CARD, PJ
    CHEN, CH
    CHENEVERT, RB
    FLIRI, A
    FROBEL, K
    GAIS, HJ
    GARRATT, DG
    HAYAKAWA, K
    HEGGIE, W
    HESSON, DP
    HOPPE, D
    HOPPE, I
    HYATT, JA
    IKEDA, D
    JACOBI, PA
    KIM, KS
    KOBUKE, Y
    KOJIMA, K
    KROWICKI, K
    LEE, VJ
    LEUTERT, T
    MALCHENKO, S
    MARTENS, J
    MATTHEWS, RS
    ONG, BS
    PRESS, JB
    RAJANBABU, TV
    ROUSSEAU, G
    SAUTER, HM
    SUZUKI, M
    TATSUTA, K
    TOLBERT, LM
    TRUESDALE, EA
    UCHIDA, I
    UEDA, Y
    UYEHARA, T
    VASELLA, AT
    VLADUCHICK, WC
    WADE, PA
    WILLIAMS, RM
    WONG, HNC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) : 3215 - 3217
  • [39] TOTAL SYNTHESIS OF HUNTERIA ALKALOIDS - STEREOCHEMICAL CONSIDERATIONS AND A TOTAL SYNTHESIS OF (+-)-VINCAMINOL
    CASTEDO, L
    HARLEYMA.J
    LEENEY, TJ
    CHEMICAL COMMUNICATIONS, 1968, (19) : 1186 - +
  • [40] REGIOCONTROLLED TOTAL SYNTHESIS OF IMERUBRINE - THE FIRST TOTAL SYNTHESIS OF A TROPOLOISOQUINOLINE ALKALOID
    BANWELL, MG
    IRELAND, NK
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (05) : 591 - 592
12345