Toward the Total Synthesis of Amphidinolide N: Synthesis of the C8-C29 Fragment

被引:11
|
作者
Kawashima, Yuki [1 ]
Toyoshima, Atsushi [1 ]
Fuwa, Haruhiko [1 ]
Sasaki, Makoto [1 ]
机构
[1] Tohoku Univ, Grad Sch Life Sci, Aoba Ku, 2-1-1 Katahira, Sendai, Miyagi 9808577, Japan
基金
日本学术振兴会;
关键词
CARIBENOLIDE-I STRUCTURES; SECONDARY ALCOHOLS; OLEFIN METATHESIS; ANTITUMOR MACROLIDE; SELECTIVE OXIDATION; PROPOSED STRUCTURE; DIRECT CONVERSION; ENOL ETHERS; RING; STRATEGY;
D O I
10.1021/acs.orglett.6b00871
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthesis of the C8-C29 fragment of amphidinolide N, a potent cytotoxic macrolide isolated from the marine dinoflagellate Amphidinium sp., has been achieved. The key features of the synthesis involve a convergent union of the C9-C15 and C16-C29 fragments by Steglich esterification and the construction of a pyran unit through a Tebbe methylenation/ring-closing metathesis sequence.
引用
收藏
页码:2232 / 2235
页数:4
相关论文
共 50 条
  • [31] Synthetic studies toward amphidinolide B1:: Synthesis of the C9-C26 fragment
    Zhang, W
    Carter, RG
    ORGANIC LETTERS, 2005, 7 (19) : 4209 - 4212
  • [32] Studies directed toward the total synthesis of scytophycin C: Synthesis of the C(1)-C(18) fragment of scytophycin C
    Grieco, PA
    Speake, JD
    TETRAHEDRON LETTERS, 1998, 39 (11) : 1275 - 1278
  • [33] Toward the total synthesis of Scleritodermin A:: preparation of the C1-N15 fragment
    Sellanes, Diver
    Manta, Eduardo
    Serra, Gloria
    TETRAHEDRON LETTERS, 2007, 48 (10) : 1827 - 1830
  • [34] Convergent Synthesis of the C1-C29 Framework of Amphidinolide F
    Romiti, Filippo
    Decultot, Ludovic
    Clark, J. Stephen
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (12): : 8126 - 8141
  • [35] Studies towards the total synthesis of Tedanolide: Synthesis of C8-C17 fragment
    Nyavanandi, Vijay Kumar
    Nanduri, Srinivas
    Andra, Naidu
    Iqbal, Javed
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3106 - U3106
  • [36] Toward the total synthesis of bryostatin 1: Synthesis of the northern fragment (C1-C16)
    Seradj, Hassan
    Voight, Eric A.
    Burke, Steven D.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [37] Studies directed toward the total synthesis of kabiramide C: Asymmetric synthesis of the C7-C19 fragment
    Liu, P
    Panek, JS
    TETRAHEDRON LETTERS, 1998, 39 (34) : 6143 - 6146
  • [38] Synthesis of the C1-C12 fragment of amphidinolide T1
    Abbineni, Chandrasekhar
    Sasmal, Pradip K.
    Mukkanti, K.
    Iqbal, Javed
    TETRAHEDRON LETTERS, 2007, 48 (24) : 4259 - 4262
  • [39] Progress toward the total synthesis of amphidinolide-A.
    Yu, Y
    Williard, PG
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U197 - U197
  • [40] Studies toward the total synthesis of tedanolide: stereoselective synthesis of the C(8)-C(17) segment
    Nyavanandi, Vijay Kumar
    Nanduri, Srinivas
    Dev, R. Vasu
    Naidu, Andra
    Iqbal, Javed
    TETRAHEDRON LETTERS, 2006, 47 (37) : 6667 - 6672