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
  • [41] TOTAL SYNTHESIS OF ERYTHROMYCINS .5. TOTAL SYNTHESIS OF ERYTHRONOLIDE-A
    COREY, EJ
    HOPKINS, PB
    KIM, S
    YOO, S
    NAMBIAR, KP
    FALCK, JR
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (23) : 7131 - 7134
  • [42] TOTAL SYNTHESIS OF STEROIDS .I. TOTAL SYNTHESIS OF RACEMIC EQUILENINE
    HOREAU, A
    LORTHIOY, E
    GUETTE, JP
    COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES SERIE C, 1969, 269 (10): : 558 - &
  • [43] STUDIES ON THE TOTAL SYNTHESIS OF OXETANOCIN .2. TOTAL SYNTHESIS OF OXETANOCIN
    NIITSUMA, S
    ICHIKAWA, Y
    KATO, K
    TAKITA, T
    TETRAHEDRON LETTERS, 1987, 28 (40) : 4713 - 4714
  • [44] First stereoselective total synthesis of pectinolide C and total synthesis of pectinolide A
    Sabitha, Gowravaram
    Das, Sukant Kishore
    AnkiReddy, Praveen
    Yadav, J. S.
    TETRAHEDRON LETTERS, 2013, 54 (09) : 1097 - 1099
  • [45] First total synthesis of Brevipolide N and total synthesis of Brevipolide M
    Raju, Kasa Shiva
    Sabitha, Gowravaram
    TETRAHEDRON LETTERS, 2018, 59 (48) : 4213 - 4215
  • [46] The first stereoselective and the total synthesis of Leiocarpin C and total synthesis of (+)-Goniodiol
    Yadav, J. S.
    Premalatha, K.
    Harshavardhan, S. J.
    Reddy, B. V. Subba
    TETRAHEDRON LETTERS, 2008, 49 (48) : 6765 - 6767
  • [47] Stereoselective Total Synthesis of Stagonolide C and Formal Total Synthesis of Modiolide A
    Mohapatra, Debendra K.
    Dash, Uttam
    Naidu, P. Ramesh
    Yadav, J. S.
    SYNLETT, 2009, (13) : 2129 - 2132
  • [48] TOTAL SYNTHESIS OF POLYCYCLIC TRITERPENES - TOTAL SYNTHESIS OF (+)-ALPHA-ONOCERIN
    STORK, G
    MEISELS, A
    DAVIES, JE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (21) : 3419 - &
  • [49] Asymmetric total synthesis and formal total synthesis of the antitumor sesquiterpenoid (+)-eremantholide A
    Li, Yi
    Hale, Karl J.
    ORGANIC LETTERS, 2007, 9 (07) : 1267 - 1270
  • [50] A concise synthesis of (±) and a total synthesis of (+)-epiquinamide
    Tong, Sok Teng
    Barker, David
    TETRAHEDRON LETTERS, 2006, 47 (29) : 5017 - 5020
12345