Formal and total synthesis of (±)-cycloclavine

被引：20
|
作者：
Jabre, Nitinkumar D. [1 ]
Watanabe, Teruki [1 ]
Brewer, Matthias [1 ]
机构：
[1] Univ Vermont, Burlington, VT 05405 USA
来源：
TETRAHEDRON LETTERS | 2014年 / 55卷 / 01期
基金：
美国国家卫生研究院; 美国国家科学基金会;
关键词：
Cycloclavine; Ergot alkaloid; Natural product synthesis; Ring fragmentation; 1,3-Dipolar cycloaddition; CHIRAL ALLYLIC ALCOHOLS; ERGOT ALKALOIDS; CYCLOPROPANATION; REAGENT; ACCESS; ACID;
D O I：
10.1016/j.tetlet.2013.10.152
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A ring fragmentation and intramolecular azomethine ylide 1,3-dipolar cycloaddition sequence of reactions was successfully used in the preparation of a known (+/-)-cycloclavine precursor in good overall yield. Results of efforts to incorporate the tetrasubstituted cyclopropane ring present in cycloclavine are also discussed. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：197 / 199
页数：3
相关论文
共 50 条
  • [21] Formal total synthesis of aspergillide A
    Izuchi, Yuko
    Kanomata, Nobuhiro
    Koshino, Hiroyuki
    Hongo, Yayoi
    Nakata, Tadashi
    Takahashi, Shunya
    TETRAHEDRON-ASYMMETRY, 2011, 22 (02) : 246 - 251
  • [22] Formal total synthesis of Palmerolide A
    Jena, Bighnanshu K.
    Mohapatra, Debendra K.
    TETRAHEDRON, 2015, 71 (34) : 5678 - 5692
  • [23] A Formal Total Synthesis of (±)-Rishitinol
    Marrugo, Kelly P.
    Maldonado, Alexis
    Banerjee, Ajoy K.
    Cabrera, Elvia, V
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2020, 52 (05) : 442 - 445
  • [24] Formal total synthesis of fostriecin
    Wang, YG
    Kobayashi, Y
    ORGANIC LETTERS, 2002, 4 (26) : 4615 - 4618
  • [25] FORMAL TOTAL SYNTHESIS OF (±)-STRICTAMINE
    Sato, Keigo
    Takanashi, Noriyuki
    Kogure, Noriyuki
    Kitajima, Mariko
    Takayama, Hiromitsu
    HETEROCYCLES, 2018, 97 (01) : 365 - 382
  • [26] Formal total synthesis of (+)-gephyrotoxin
    Santarem, Marco
    Vanucci-Bacque, Corinne
    Lhommet, Gerard
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (16): : 6466 - 6469
  • [27] A formal total synthesis of (-)-dysiherbaine
    Kang, SH
    Lee, YM
    SYNLETT, 2003, (07) : 993 - 994
  • [28] A FORMAL TOTAL SYNTHESIS OF APLYSIN
    KHER, SM
    KULKARNI, GH
    SYNTHETIC COMMUNICATIONS, 1990, 20 (08) : 1241 - 1247
  • [29] Formal total synthesis of (+)-methynolide
    Cossy, J
    Bauer, D
    Bellosta, V
    SYNLETT, 2002, (05) : 715 - 718
  • [30] Formal total synthesis of (-)-exiguolide
    Reddy, Chada Raji
    Rao, Nagavaram Narsimha
    RSC ADVANCES, 2012, 2 (20) : 7724 - 7734
12345