Synthetic studies toward the total synthesis of tedanolide: assembly of the C1-C23 carbon backbone

被引:16
|
作者
Wong, Chek-Ming [1 ]
Loh, Teck-Peng [1 ]
机构
[1] Nanyang Technol Univ, Div Chem & Biol Chem, Singapore 639716, Singapore
关键词
tedanolide; stereoselective; aldol; boron reagent; fragment assembly;
D O I
10.1016/j.tetlet.2006.04.044
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A stereoselective assembly of the C1-C23 fragment representing the carbon backbone of tedanolide was accomplished utilizing a chiral boron reagent to effect the aldol coupling of the C1-C12 diketoester fragment with the C13-C23 aldehyde fragment. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4485 / 4489
页数:5
相关论文
共 50 条
  • [31] Synthetic studies toward the total synthesis of swinholide.: 1.: Stereoselective construction of the C19-C35 subunit
    Keck, GE
    Lundquist, GD
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12): : 4482 - 4491
  • [32] Stereochemically Versatile Synthesis of the C1-C12 Fragment of Tedanolide C
    Smith, Thomas E.
    Fink, Sarah J.
    Levine, Zebulon G.
    McClelland, Kerani A.
    Zackheim, Adrian A.
    Daub, Mary E.
    ORGANIC LETTERS, 2012, 14 (06) : 1452 - 1455
  • [33] Studies toward the total synthesis of inostamycin C.
    Fuller, NO
    Morken, JP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U129 - U129
  • [34] Studies toward the total synthesis of eurycolactone C.
    Seo, YH
    Kraus, GA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U223 - U223
  • [35] Studies toward Total Synthesis of Divergolides C and D
    Rasapalli, Slvappa
    Jarugumilli, Gopalakrishna
    Yarrapothu, Gangadhara Rao
    Golen, James A.
    Rheingold, Arnold L.
    ORGANIC LETTERS, 2013, 15 (07) : 1736 - 1739
  • [36] Studies toward a total synthesis of amphidinolide C.
    Shotwell, JB
    Roush, WR
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U152 - U152
  • [37] Studies toward the total synthesis of gambieric acids A and C: Convergent assembly of the nonacyclic polyether skeleton
    Sato, Kazushi
    Sasaki, Makoto
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (14) : 2518 - 2522
  • [38] Studies towards the synthesis of tedanolide C. Construction of the C13-epi C1-C15 fragment
    Zambrana, Joana
    Romea, Pedro
    Urpi, Felix
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (23) : 5219 - 5223
  • [39] Studies directed toward the total synthesis of discodermolide: Asymmetric synthesis of the C1-C14 fragment
    Arefolov, A
    Panek, JS
    ORGANIC LETTERS, 2002, 4 (14) : 2397 - 2400
  • [40] Synthesis of the C.1 to C.11 fragment of tedanolide.
    Jung, ME
    Lee, CP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U226 - U226