71443-22-6Relevant academic research and scientific papers
Expeditious metal-free access to functionalized polycyclic acetals under mild aqueous conditions
Kasare, Sanghratna,Bankar, Siddheshwar K.,Ramasastry
, p. 4284 - 4287 (2014)
A facile approach for the synthesis of furopyrans and bicyclic bisacetals under mild aqueous conditions is described. This potentially green, diversity oriented approach involves cascade Michael addition and cycloacetalization of pyranones and 1,3-dicarbo
Enantioselective 1,3-Dipolar [6+4] Cycloaddition of Pyrylium Ions and Fulvenes towards Cyclooctanoids
McLeod, David,Cherubini-Celli, Alessio,Sivasothirajah, Nisanhi,McCulley, Christina H.,Christensen, Mette Louise,J?rgensen, Karl Anker
supporting information, p. 11417 - 11422 (2020/08/06)
Organocatalytic enantioselective 1,3-dipolar [6+4] cycloadditions of pyrylium ion intermediates with fulvenes promoted by a chiral primary amine catalyst have been developed to proceed in moderate to good yields and high enantioselectivities. The resultant chiral bicyclo[6.3.0]undecane scaffold containing a transannular bridging ether is densely functionalised providing a rigid scaffold for further manipulations. Computational studies give important insights into the role of the primary amine catalyst. Analysis of the reaction shows that the catalytic reaction proceeds in a step-wise manner and rationalises the stereochemical outcome of the reaction. Several stereoselective complexity-generating transformations, facilitated by the diverse functional groups and transannular bridge, are presented, highlighting the versatility of the core towards a number of the cyclooctanoid natural products.
Palladium-Catalyzed [3 + 2]-C-C/N-C Bond-Forming Annulation
Liu, Yang,Mao, Zhongyi,Pradal, Alexandre,Huang, Pei-Qiang,Oble, Julie,Poli, Giovanni
supporting information, p. 4057 - 4061 (2018/07/15)
The synthesis of bi- and tricyclic structures incorporating pyrrolidone rings is disclosed, starting from resonance-stabilized acetamides and cyclic α,β-unsaturated-γ-oxycarbonyl derivatives. This process involves an intermolecular Tsuji-Trost allylation/intramolecular nitrogen 1,4-addition sequence. Crucial for the success of this bis-nucleophile/bis-electrophile [3 + 2] annulation is its well-defined step chronology in combination with the total chemoselectivity of the former step. When the newly formed annulation product carries a properly located o-haloaryl moiety at the nitrogen substituent, a further intramolecular keto α-arylation can join the cascade, thereby forming two new cycles and three new bonds in the same synthetic operation.
Discovery of inhibitors of the wnt and hedgehog signaling pathways through the catalytic enantioselective synthesis of an iridoid-inspired compound collection
Takayama, Hiroshi,Jia, Zhi-Jun,Kremer, Lea,Bauer, Jonathan O.,Strohmann, Carsten,Ziegler, Slava,Antonchick, Andrey P.,Waldmann, Herbert
supporting information, p. 12404 - 12408 (2013/12/04)
Cousins you can count on: An iridoid-inspired compound collection was synthesized efficiently by the resolution of cyclic enones in an asymmetric cycloaddition with azomethine ylides. The collection contained novel potent inhibitors of the Wnt and Hedgehog signaling pathways. Copyright
The Intramolecular Enyne Diels-Alder Reaction. Stereoselective Construction of Tricyclic Dioxadienones and Mechanistic Outline
Hoffmann, H. M. R.,Krumwiede, D.,Mucha, B.,Oehlerking, H. H.,Prahst, G. W.
, p. 8999 - 9018 (2007/10/02)
4-Methylpent-4-en-2-yn-1-ols and 6-hydroxy-2,3-dihydro-6H-pyran-3-ones are condensed in different ways to a series of tricyclic dioxadienones which contain the basic framework of the cadlinolides A mechanism of the intramolecular enyne-ene cycloisomerization and the origin of the resulting type I and type II dienes is proposed.
