Enantioselective Total Synthesis of the Cephalotaxus Alkaloid (-)-Cephalotine A

被引：4
作者：
Sheng, Peng-Zhen [1 ,2 ]
Li, Lu-Lu [1 ]
Ni, Zhi-Bin [1 ,2 ]
Wei, Kun [1 ]
Yang, Yu-Rong [1 ]
机构：
[1] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
ORGANIC LETTERS | 2023年
基金：
中国国家自然科学基金;
关键词：
FORMAL TOTAL-SYNTHESIS; ALPHA-ALLYLATION; UNIFIED STRATEGY; NATURAL-PRODUCTS; GAMMA-LACTAMS; HECK REACTION; (+/-)-CEPHALOTAXINE; REARRANGEMENT; CONSTRUCTION; CYCLIZATION;
D O I：
10.1021/acs.orglett.3c02097
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Cephalotine A, a recently isolated Cephalotaxus alkaloid,was firstsynthesized enantioselectively through three critical reactions. SmI2 -mediated radical cyclization of lactone and aldehyde toforge the final ring system, Chang's iridium-catalyzed C-Hamidation to construct pyrrolidone stereoselectively, and Carreria'sdual Ir/amine catalyzed allylation to install the vicinal tertiarystereocenters.
引用
收藏
页码：7459 / 7463
页数：5
相关论文
共 50 条
  • [21] Enantioselective Total Synthesis of (-)-Martinellic Acid
    Pappoppula, Mukesh
    Aponick, Aaron
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (52) : 15827 - 15830
  • [22] Enantioselective Total Synthesis of (+)-Propolisbenzofuran B
    Xu, Wen-Xiu
    Zhao, Li-Han
    Zhu, Yao
    Lu, Hai-Hua
    CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (22) : 2833 - 2839
  • [23] An enantioselective biomimetic total synthesis of (-)-siccanin
    Trost, BM
    Shen, HC
    Surivet, JP
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (33) : 3943 - 3947
  • [24] Total Synthesis of the Tetracyclic Antimalarial Alkaloid (±)-Myrioneurinol
    Nocket, Anthony J.
    Weinreb, Steven M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (51) : 14162 - 14165
  • [25] Total Synthesis of the Monoterpenoid Indole Alkaloid (±)-Aspidophylline A
    Teng, Mingxing
    Zi, Weiwei
    Ma, Dawei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (07) : 1814 - 1817
  • [26] Asymmetric Total Synthesis of a Pentacyclic Lycopodium Alkaloid: Huperzine-Q
    Nakayama, Atsushi
    Kogure, Noriyuki
    Kitajima, Mariko
    Takayama, Hiromitsu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (35) : 8025 - 8028
  • [27] Cephalofortunone, a structurally unique Cephalotaxus alkaloid from Cephalotaxus fortune Hook f.
    Li, Hanxiang
    Wen, Yanhua
    Wang, Feifei
    Wu, Ping
    Wei, Xiaoyi
    TETRAHEDRON LETTERS, 2015, 56 (42) : 5735 - 5737
  • [28] Enantioselective Total Synthesis of Terreumols A and C from the Mushroom Tricholoma terreum
    Frichert, Alex
    Jones, Peter G.
    Lindel, Thomas
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (08) : 2916 - 2919
  • [29] Enantioselective Total Synthesis of (-)-FR182877
    Suzuki, Natsumi Tanaka
    Suzuki, Takahiro
    Matsumura, Takehiko
    Hosoya, Yousuke
    Nakazato, Tomoyuki
    Nakada, Masahisa
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2011, 69 (06) : 646 - 660
  • [30] Enantioselective Total Synthesis of Pinnaic Acid and Halichlorine
    Xu, Shu
    Unabara, Daisuke
    Uemura, Daisuke
    Arimoto, Hirokazu
    CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (01) : 367 - 375
12345