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 58 条
  • [11] Convergent Total Syntheses of Callipeltosides A, B, and C
    Frost, James R.
    Pearson, Colin M.
    Snaddon, Thomas N.
    Booth, Richard A.
    Ley, Steven V.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (37) : 9366 - 9371
  • [12] An efficient strategy for the synthesis of endocyclic enol ethers and its application to the synthesis of spiroacetals
    Fuwa, Haruhiko
    Sasaki, Makoto
    [J]. ORGANIC LETTERS, 2008, 10 (12) : 2549 - 2552
  • [13] Total Synthesis and Complete Stereostructure of Gambieric Acid A
    Fuwa, Haruhiko
    Ishigai, Kazuya
    Hashizume, Keisuke
    Sasaki, Makoto
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (29) : 11984 - 11987
  • [14] A practical and efficient synthesis of the C-16-C-28 spiroketal fragment (CD) of the spongistatins
    Gaunt, MJ
    Hook, DF
    Tanner, HR
    Ley, SV
    [J]. ORGANIC LETTERS, 2003, 5 (25) : 4815 - 4818
  • [15] A short synthetic pathway to a fully-functionalized southern hemisphere of the antitumor macrolide bryostatin 1
    Hale, KJ
    Frigerio, M
    Manaviazar, S
    [J]. ORGANIC LETTERS, 2001, 3 (23) : 3791 - 3794
  • [16] Higashibayashi S, 2000, SYNLETT, P1306
  • [17] Diastereoselective synthesis of the C(17)-C(28) fragment (The C-D spiroketal unit) of spongistatin 1 (altohyrtin A) via a kinetically controlled iodo-spiroketalization reaction
    Holson, EB
    Roush, WR
    [J]. ORGANIC LETTERS, 2002, 4 (21) : 3719 - 3722
  • [18] CARBONYL ADDITION-REACTIONS PROMOTED BY CERIUM REAGENTS
    IMAMOTO, T
    [J]. PURE AND APPLIED CHEMISTRY, 1990, 62 (04) : 747 - 752
  • [19] REACTIONS OF CARBONYL-COMPOUNDS WITH GRIGNARD-REAGENTS IN THE PRESENCE OF CERIUM CHLORIDE
    IMAMOTO, T
    TAKIYAMA, N
    NAKAMURA, K
    HATAJIMA, T
    KAMIYA, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) : 4392 - 4398
  • [20] CARBON CARBON BOND-FORMING REACTIONS USING CERIUM METAL OR ORGANOCERIUM(III) REAGENTS
    IMAMOTO, T
    KUSUMOTO, T
    TAWARAYAMA, Y
    SUGIURA, Y
    MITA, T
    HATANAKA, Y
    YOKOYAMA, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21) : 3904 - 3912