Studies of the Asymmetric Total Synthesis of Clavilactone D by the 'Lariat' Cyclization Strategy

被引:11
|
作者
Yoshimitsu, Takehiko [1 ]
Nojima, Shoji [1 ]
Hashimoto, Masashi [1 ]
Tsukamoto, Koji [1 ]
Tanaka, Tetsuaki [1 ]
机构
[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan
来源
SYNTHESIS-STUTTGART | 2009年 / 17期
关键词
total synthesis; natural products; cyclizations; asymmetric synthesis; alkylations; ORGANIC-SYNTHESIS; STRUCTURE ELUCIDATION; RADICAL REACTIONS; INDIUM METAL;
D O I
10.1055/s-0029-1216909
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A route to the core structure of clavilactone D, a new member of the tyrosine kinase inhibitors, is reported. The route employs sequential cyclization initiated by iodo etherification followed by Friedel-Crafts cyclization to furnish a polycyclic lactone fused with an aromatic ring, which is readily transformed into the proposed clavilactone scaffold.
引用
收藏
页码:2963 / 2969
页数:7
相关论文
共 50 条
  • [21] Total Synthesis of (+)-Neopeltolide by the Macrocyclization/Transannular Pyran Cyclization Strategy
    Nakazato, Kazuki
    Oda, Mami
    Fuwa, Haruhiko
    ORGANIC LETTERS, 2022, 24 (22) : 4003 - 4008
  • [22] Total Synthesis of (-)-Enigmazole A by the Macrocyclization/Transannular Pyran Cyclization Strategy
    Masuda, Taisei
    Ohyama, Kyoya
    Yoshimura, Atsushi
    Fuwa, Haruhiko
    ORGANIC LETTERS, 2024, 26 (10) : 2045 - 2050
  • [23] Total Synthesis of (-)-Graminin A Based on Asymmetric Cyclization Carbonylation of Propargyl Acetate
    Ito, Yoichi
    Kusakabe, Taichi
    Dhage, Yogesh Daulat
    Takahashi, Keisuke
    Sakata, Ken
    Sasai, Hiroaki
    Kato, Keisuke
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (24): : 16268 - 16277
  • [24] Thiolate-mediated reductive cyclization: asymmetric total synthesis of (+)-engelharquinone
    Ando, Yoshio
    Fukazawa, Takumi
    Hori, Subaru
    Ohmori, Ken
    Suzuki, Keisuke
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2019, 194 (07) : 723 - 725
  • [25] Asymmetric Total Synthesis of Gymnothespirolignan A via a Bioinspired Double Cyclization Approach
    Yang, Hao
    Qin, Zhengyi
    Liang, Xinyu
    Yang, Yuting
    Xue, Yage
    Duan, Yaxuan
    Wang, Min
    Zhang, Zhiyu
    Li, Huilin
    She, Xuegong
    JOURNAL OF ORGANIC CHEMISTRY, 2025, 90 (10): : 3719 - 3726
  • [26] Asymmetric Total Synthesis of Dankasterones A and B and Periconiastone A Through Radical Cyclization
    Chen, Pengquan
    Wang, Cheng
    Yang, Rui
    Xu, Hongjin
    Wu, Jinghua
    Jiang, Huanfeng
    Chen, Kai
    Ma, Zhiqiang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (10) : 5512 - 5518
  • [27] STEREOSELECTIVE CYCLIZATION AND TOTAL SYNTHESIS OF GERMACRENE-D
    NISHIMURA, H
    HASEGAWA, H
    KOYAMA, Y
    NAKANO, H
    SEO, A
    MIZUTANI, J
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1979, (APR): : 53 - 53
  • [28] Asymmetric Total Synthesis of Soraphen A: A Flexible Alkyne Strategy
    Trost, Barry M.
    Sieber, Joshua D.
    Qian, Wei
    Dhawan, Rajiv
    Ball, Zachary T.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (30) : 5478 - 5481
  • [29] Studies toward the asymmetric total synthesis of oxazolomycin
    O'Riordan, Timothy J. C.
    Donohoe, Timothy J.
    Slater, Martin J.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 236
  • [30] Studies towards the asymmetric total synthesis of the Phomoidrides
    Castagner, B
    Leighton, JL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U236 - U236