Diastereoselective total synthesis of (±)-schindilactone a, Part 3: The final phase and completion.
作者： Wei-Wu Ren , Zhi-Xing Chen , Qing Xiao , Yong Li , Tian-Wen Sun
关键词: Cyclopentenone 、 Chemistry 、 Total synthesis 、 Diene 、 Vinyl bromide 、 Coupling reaction 、 Combinatorial chemistry 、 Catalysis 、 Annulation 、 Stereochemistry 、 Ring (chemistry)
摘要: The final phase for the total synthesis of (±)-schindilactone A (1) is described herein. Two independent synthetic approaches were developed that featured Pd-thiourea-catalyzed cascade carbonylative annulation reactions to construct intermediate 3 and a RCM reaction make 4. Other important steps enabled completion included: 1) Ag-mediated ring-expansion form vinyl bromide 17 from dibromocyclopropane 30; 2) Pd-catalyzed coupling with copper enolate synthesize ketoester 16; 3) generate oxabicyclononenol 10 diene 11; 4) cyclopentenone fragment in substrate 8 was constructed through Co-thiourea-catalyzed Pauson-Khand (PKR); 5) Dieckmann-type condensation successfully ring schindilactone (1). chemistry will shed light on other family members A.
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sci-hub.se 参考文章(50)
Kazuaki Ishihara, Manabu Kubota, Hideki Kurihara, Hisashi Yamamoto, Scandium Trifluoromethanesulfonate as an Extremely Active Lewis Acid Catalyst in Acylation of Alcohols with Acid Anhydrides and Mixed Anhydrides. Journal of Organic Chemistry. ,vol. 61, pp. 4560- 4567 ,(1996) , 10.1021/JO952237X
Hong Myung Lee, Cristina Nieto-Oberhuber, Matthew D. Shair, Enantioselective synthesis of (+)-cortistatin a, a potent and selective inhibitor of endothelial cell proliferation. Journal of the American Chemical Society. ,vol. 130, pp. 16864- 16866 ,(2008) , 10.1021/JA8071918
Alexandros L. Zografos, Athanasios Yiotakis, Dimitris Georgiadis, Rapid access to the tricyclic spirotetronic core of abyssomicins. Organic Letters. ,vol. 7, pp. 4515- 4518 ,(2005) , 10.1021/OL051872E
Yefeng Tang, Lujiang Deng, Yandong Zhang, Guangbin Dong, Jiahua Chen, Zhen Yang, Tetramethyl thiourea/Co-2(CO)(8)-catalyzed Pauson-Khand reaction under balloon pressure of CO Organic Letters. ,vol. 7, pp. 593- 595 ,(2005) , 10.1021/OL047651A
Mario A. Tan, Mariko Kitajima, Noriyuki Kogure, Maribel G. Nonato, Hiromitsu Takayama, Isolation and total syntheses of two new alkaloids, dubiusamines-A, and -B, from Pandanus dubius Tetrahedron. ,vol. 66, pp. 3353- 3359 ,(2010) , 10.1016/J.TET.2010.02.073
Gary H. Posner, John P. Maxwell, Mehmet Kahraman, Mild, Fast, and Stereoselective Epoxide Opening by Ketone Enolate Anions. Application to Synthesis of the Norlignan Curculigine Journal of Organic Chemistry. ,vol. 68, pp. 3049- 3054 ,(2003) , 10.1021/JO020744Q
Takao Sakamoto, Yoshinori Kondo, Kaoru Masumoto, Hiroshi Yamanaka, Palladium-catalysed arylation of α-methoxyketene methyl silyl acetals J. Chem. Soc., Perkin Trans. 1. pp. 235- 236 ,(1994) , 10.1039/P19940000235
Sílvia Fonquerna, Albert Moyano, Miquel A. Pericàs, Antoni Riera, A convenient preparation of N-(2-alkynoyl) derivatives of chiral oxazolidin-2-ones and bornane-10,2-sultam Tetrahedron-asymmetry. ,vol. 8, pp. 1685- 1691 ,(1997) , 10.1016/S0957-4166(97)00167-5
Roberta Galarini, Alfredo Musco, Roberto Pontellini, Roberto Santi, Asymmetric synthesis of alkyl 2-arylalkanoates by cross-coupling reactions cabled by Pd complexes Journal of Molecular Catalysis. ,vol. 72, ,(1992) , 10.1016/0304-5102(92)85001-V
N. Vijaya Ganesh, N. Jayaraman, Synthesis of septanosides through an oxyglycal route. Journal of Organic Chemistry. ,vol. 72, pp. 5500- 5504 ,(2007) , 10.1021/JO070444E