Enantioselective total synthesis of (+)-galbulin via organocatalytic domino Michael-Michael-aldol condensation

被引：35
|
作者：
Hong, Bor-Cherng [1 ]
Hsu, Che-Sheng [1 ]
Lee, Gene-Hsiang [2 ]
机构：
[1] Natl Chung Cheng Univ, Dept Chem & Biochem, Chiayi 621, Taiwan
[2] Natl Taiwan Univ, Instrumentat Ctr, Taipei 106, Taiwan
来源：
CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 18期
关键词：
ASYMMETRIC-SYNTHESIS; CASCADE REACTIONS; NATURAL-PRODUCTS; LIGNANS; ANALOGS; EPIPODOPHYLLOTOXIN; STEREOCHEMISTRY; PODOPHYLLOTOXIN; (+/-)-GALBULIN; CHEMISTRY;
D O I：
10.1039/c2cc16682h
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A concise and practical enantioselective synthesis of (+)-galbulin has been achieved using organocatalytic domino Michael-Michael-aldol condensation and organocatalytic kinetic resolution as the key steps.
引用
收藏
页码：2385 / 2387
页数：3
相关论文
共 50 条
  • [31] Asymmetric synthesis of polysubstituted chiral chromans via an organocatalytic oxa-Michael-nitro-Michael domino reaction
    Tang, Cheng-Ke
    Feng, Kai-Xiang
    Xia, Ai-Bao
    Li, Chen
    Zheng, Ya-Yun
    Xu, Zhen-Yuan
    Xu, Dan-Qian
    [J]. RSC ADVANCES, 2018, 8 (06): : 3095 - 3098
  • [32] Organocatalytic Domino Michael-Aldol Reaction of Ketones and α,β-Unsaturated Trifluoromethyl Ketones
    Wang, Xiao-Jin
    Zhao, Yan
    Liu, Jin-Tao
    [J]. SYNTHESIS-STUTTGART, 2008, Georg Thieme Verlag (24): : 3967 - 3973
  • [33] Organocatalytic Asymmetric Synthesis of Tetracyclic Pyridocarbazole Derivatives by Using a Diels-Alder/aza-Michael/Aldol Condensation Domino Reaction
    Enders, Dieter
    Joie, Celine
    Deckers, Kristina
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (33) : 10818 - 10821
  • [34] Enantioselective Synthesis of Spiro[1,3-indanedione-tetrahydrothiophene]s by Organocatalytic Sulfa-Michael/Michael Domino Reaction
    Duan, Jindian
    Cheng, Jing
    Li, Bing
    Qi, Fei
    Li, Pengfei
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (28) : 6130 - 6134
  • [35] Organocatalytic enantioselective Michael and hetero-Michael reactions
    Vicario, Jose L.
    Badia, Dolores
    Carrillo, Luisa
    [J]. SYNTHESIS-STUTTGART, 2007, (14): : 2065 - 2092
  • [36] Organocatalytic enantioselective cascade Michael-Aldol condensation reactions: Efficient assembly of densely functionalized chiral cyclopentenes
    Wang, Jian
    Li, Hao
    Xie, Hexin
    Zu, Liansuo
    Shen, Xu
    Wang, Wei
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (47) : 9050 - 9053
  • [37] Catalytic enantioselective domino oxa-Michael/aldol condensations:: Asymmetric synthesis of benzopyran derivatives
    Sunden, Henrik
    Ibrahem, Ismail
    Zhao, Gui-Ling
    Eriksson, Lars
    Cordova, Armando
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (02) : 574 - 581
  • [38] Asymmetric Organocatalytic Synthesis of Highly Functionalized Spirocyclohexane Indandiones via a One-Pot Michael/Michael/Aldol Sequence
    Bluemel, Marcus
    Chauhan, Pankaj
    Vermeeren, Cornelia
    Dreier, Angelika
    Lehmann, Christian
    Enders, Dieter
    [J]. SYNTHESIS-STUTTGART, 2015, 47 (22): : 3618 - 3628
  • [39] ORGN 596-Enantioselective organocatalytic tandem Michael-aldol reactions
    Li, Hao
    Wang, Jian
    Zu, Liansuo
    Xie, Hexin
    Jiang, Wei
    Wang, Wei
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 235
  • [40] Enantioselective synthesis of the tetrahydro-6H-benzo[c]chromenes via Domino Michael-Aldol condensation: control of five stereocenters in a quadruple-cascade organocatalytic multi-component reaction
    Kotame, Prakash
    Hong, Bor-Cherng
    Liao, Ju-Hsiou
    [J]. TETRAHEDRON LETTERS, 2009, 50 (06) : 704 - 707
12345