Acid-catalyzed aza-diels-alder reactions for the total synthesis of (±)-lapatin B

被引：27
|
作者：
Leca, Dominique [1 ]
Gaggini, Francesca [1 ]
Cassayre, Jerome [1 ]
Loiseleur, Olivier [1 ]
Pieniazek, Susan N. [1 ]
Luft, Jennifer A. R. [1 ]
Houk, K. N. [1 ]
机构：
[1] SYNGENTA Crop Protect AG, Res Chem, CH-4002 Basel, Switzerland
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 11期
关键词：
D O I：
10.1021/jo0705162
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A 5-step total synthesis of microfungal alkaloid (+/-)-lapatin B has been accomplished via a key 2-aza-Diels-Alder reaction. Bronsted acids catalyze the cycloaddition step and provide improved exo selectivity. This synthetic route has been applied to the construction of related spiro-quinazoline structures.
引用
收藏
页码：4284 / 4287
页数：4
相关论文
共 50 条
  • [1] The Bronsted Acid-Catalyzed, Enantioselective Aza-Diels-Alder Reaction for the Direct Synthesis of Chiral Piperidones
    Weilbeer, Claudia
    Sickert, Marcel
    Naumov, Sergei
    Schneider, Christoph
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (03) : 513 - 518
  • [2] Investigation of Lewis acid-catalyzed asymmetric aza-Diels-Alder reactions of 2H-azirines
    Timén, AS
    Somfai, P
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (26): : 9958 - 9963
  • [3] Chiral Phosphoric Acid-Catalyzed Enantioselective Three- Component Aza-Diels-Alder Reactions of Aminopyrroles and Aminopyrazoles
    Brioche, Julien
    Courant, Thibaut
    Alcaraz, Lilian
    Stocks, Michael
    Furber, Mark
    Zhu, Jieping
    Masson, Geraldine
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (08) : 1719 - 1724
  • [4] Stereoselective aza-Diels-Alder reactions
    Rowland, Gerald B.
    Rowland, Emily B.
    Zhang, Qiang
    Antilla, Jon C.
    CURRENT ORGANIC CHEMISTRY, 2006, 10 (09) : 981 - 1005
  • [5] Niobium-catalyzed highly enantioselective aza-Diels-Alder reactions
    Jurcik, Vaclav
    Arai, Kenzo
    Salter, Matthew M.
    Yamashita, Yasuhiro
    Kobayashi, Shu
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (05) : 647 - 651
  • [6] Chiral Bronsted acid-catalyzed asymmetric aza Diels-Alder reactions
    Akiyama, Takahiko
    Itoh, Junji
    Fuchibe, Kohei
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [7] Synthesis of aza-Diels-Alder products
    Wolfgang, Josh
    Predecki, Daniel
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [8] Asymmetric Synthesis of Tetrahydropyridines via a BrOnsted Acid Catalyzed Aza-Diels-Alder Reaction
    Beceno, Christian
    Krappitz, Tim
    Raabe, Gerhard
    Enders, Dieter
    SYNTHESIS-STUTTGART, 2015, 47 (23): : 3813 - 3821
  • [9] Asymmetric Bronsted acid-catalyzed aza-Diels-Alder reaction of cyclic C-acylimines with cyclopentadiene
    Rueping, Magnus
    Raja, Sadiya
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 1819 - 1824
  • [10] Bronsted Acid or Solid Acid Catalyzed Aza-Diels-Alder Reactions of Methylenecyclopropanes with Ethyl (Arylimino)acetates
    Zhu, Zhi-Bin
    Shao, Li-Xiong
    Shi, Min
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (15) : 2576 - 2580
12345