Total Synthesis of (±)-Haliclonacyclamine C

被引：45
|
作者：
Smith, Brian J. [1 ,2 ]
Sulikowski, Gary A. [1 ,2 ]
机构：
[1] Vanderbilt Univ, Dept Chem, Vanderbilt Inst Chem Biol, Nashville, TN 37235 USA
[2] Vanderbilt Univ, Dept Biochem, Vanderbilt Inst Chem Biol, Nashville, TN 37235 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 09期
基金：
美国国家卫生研究院;
关键词：
alkaloids; macrocycles; natural products; ring-closing metathesis; total synthesis; RING-CLOSING METATHESIS; SPONGE HALICLONA SP; HALICYCLAMINE-A; ORGANIC-SYNTHESIS; MARINE SPONGES; ALKALOIDS; DERIVATIVES; ORIGIN; HALICLONACYCLAMINES; EPOXIDATION;
D O I：
10.1002/anie.200905732
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
"Chemical Equation Presented" (±)-Haliolonacyolamine C First In Its class: The synthesis of the tetracyclic alkylpiperidine marine alkaloid (±)-haliclonacyclamine C has been completed, with a longest linear sequence of 24 steps. The key transformations are the stereoselective hydrogenation of an unsaturated macrocyclic bis (piperidine) and a ring-closing alkyne metathesis reaction. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：1599 / 1602
页数：4
相关论文
共 50 条
  • [31] Bioinspired Total Synthesis of Sespenine
    Sun, Yu
    Chen, Pengxi
    Zhang, Deliang
    Baunach, Martin
    Hertweck, Christian
    Li, Ang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (34) : 9012 - 9016
  • [32] Concise Diverted Total Synthesis of Amphidinolide T1 and T4 from a (12E)-Cycloalkene by Selective Functionalization of the C12-C13 Double Bond
    Sun, Lijie
    Wu, Dongdong
    Wu, Jinlong
    Dai, Wei-Min
    SYNLETT, 2011, (20) : 3036 - 3040
  • [33] Total Synthesis of Camptothecins: An Update
    Chen, Lei
    Chen, Fen-Er
    SYNLETT, 2017, 28 (10) : 1134 - 1150
  • [34] Total Synthesis of Dragocins A-C through Electrochemical Cyclization
    Smith, Brendyn P.
    Truax, Nathanyal J.
    Pollatos, Alexandros S.
    Meanwell, Michael
    Bedekar, Pranali
    Garrido-Castro, Alberto F.
    Baran, Phil S.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (19)
  • [35] Toward a Total Synthesis of Divergolide A; Synthesis of the Amido Hydroquinone Core and the C10-C15 Fragment
    Zhao, Guanglian
    Wu, Jinlong
    Dai, Wei-Min
    SYNLETT, 2012, (19) : 2845 - 2849
  • [36] Total Synthesis of Thiocladospolide A and Its C2-Epimer
    Swami, Pramod
    Mali, Maruti
    Dhulshette, Baswaraj
    Ghosh, Subhash
    SYNTHESIS-STUTTGART, 2022, 54 (03): : 683 - 688
  • [37] First Total Synthesis of the Pyrrolizidine Alkaloid Amphorogynine C through Intramolecular Azide-Olefin Cycloaddition
    de Miguel, Irene
    Velado, Marina
    Herradon, Bernardo
    Mann, Enrique
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (23) : 4347 - 4353
  • [38] Total Synthesis of Damirone C, Makaluvamine O, Makaluvone, Batzelline C and Batzelline D
    Backenkoehler, Jana
    Spindler, Stefanie
    Spiteller, Peter
    CHEMISTRYSELECT, 2017, 2 (08): : 2589 - 2592
  • [39] Total Synthesis of (-)-Heliespirone A and (+)-Heliespirone C
    Norcott, Philip
    McErlean, Christopher S. P.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (23) : 5056 - 5062
  • [40] Stereoselective Total Synthesis of Polyrhacitides A and B
    Yadav, J. S.
    Rajendar, Goreti
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (33) : 6781 - 6788
12345