Stereoselective Synthesis of Hexahydro-1H-spiro[isoquinoline-4,4'-pyran] Scaffolds through an Intramolecular Prins Cascade Process.
作者： B. V. Subba Reddy , Durgaprasad Medaboina , B. Sridhar
DOI: 10.1021/JO5023926
关键词:
摘要: A novel tandem cyclization strategy has been developed for the synthesis of hexahydro-1H-spiro[isoquinoline-4,4′-pyran] derivatives through condensation 3-((benzylamino)methyl)but-3-en-1-ol with aldehydes using BF3·OEt2. The reaction proceeds in a highly stereoselective manner, leading to single diastereoisomer. This approach is simple and efficient alternative pharmacologically important spiroisoquinoline scaffolds.
acs.org
sci-hub.se 参考文章(60)
B. V. Subba Reddy, Harish Kumar, P. Sivaramakrishna Reddy, Kiran Kumar Singarapu, Prins Spirocyclization for the Synthesis of Spiro[isobenzofuran-pyran] Derivatives European Journal of Organic Chemistry. ,vol. 2014, pp. 4234- 4238 ,(2014) , 10.1002/EJOC.201402157
Michael R. Gesinski, Kwanruthai Tadpetch, Scott D. Rychnovsky, Symmetric macrocycles by a Prins dimerization and macrocyclization strategy. Organic Letters. ,vol. 11, pp. 5342- 5345 ,(2009) , 10.1021/OL9022062
Michael M.-C. Lo, Christopher S. Neumann, Satoshi Nagayama, Ethan O. Perlstein, Stuart L. Schreiber, A Library of Spirooxindoles Based on a Stereoselective Three-Component Coupling Reaction Journal of the American Chemical Society. ,vol. 126, pp. 16077- 16086 ,(2004) , 10.1021/JA045089D
En Zhang, Chun-An Fan, Yong-Qiang Tu, Fu-Min Zhang, Yan-Lin Song, Organocatalytic Asymmetric Vinylogous α-Ketol Rearrangement: Enantioselective Construction of Chiral All-Carbon Quaternary Stereocenters in Spirocyclic Diketones via Semipinacol-Type 1,2-Carbon Migration Journal of the American Chemical Society. ,vol. 131, pp. 14626- 14627 ,(2009) , 10.1021/JA906291N
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
Takehiko Iida, Hiroki Satoh, Kenji Maeda, Yuhei Yamamoto, Ken-ichi Asakawa, Naotaka Sawada, Toshihiro Wada, Chie Kadowaki, Takahiro Itoh, Toshiaki Mase, Steven A. Weissman, Dave Tschaen, Shane Krska, R. P. Volante, Practical synthesis of a neuropeptide Y antagonist via stereoselective addition to a ketene Journal of Organic Chemistry. ,vol. 70, pp. 9222- 9229 ,(2005) , 10.1021/JO0512709
Benjamin D. Cons, Adam J. Bunt, Christopher D. Bailey, Christine L. Willis, Total synthesis of (-)-blepharocalyxin D and analogues. Organic Letters. ,vol. 15, pp. 2046- 2049 ,(2013) , 10.1021/OL400736W
Stephen Michael Rajesh, Subbu Perumal, J. Carlos Menéndez, Perumal Yogeeswari, Dharmarajan Sriram, Antimycobacterial activity of spirooxindolo-pyrrolidine, pyrrolizine and pyrrolothiazole hybrids obtained by a three-component regio- and stereoselective 1,3-dipolar cycloaddition MedChemComm. ,vol. 2, pp. 626- 630 ,(2011) , 10.1039/C0MD00239A
Zhi-Hua Chen, Yong-Qiang Tu, Shu-Yu Zhang, Fu-Min Zhang, Development of the Intramolecular Prins Cyclization/Schmidt Reaction for the Construction of the Azaspiro[4,4]nonane: Application to the Formal Synthesis of (±)-Stemonamine Organic Letters. ,vol. 13, pp. 724- 727 ,(2011) , 10.1021/OL102955E
Nigel S. Simpkins, Christopher D. Gill, Asymmetric total synthesis of the proposed structure of the medicinal alkaloid jamtine using the chiral base approach. Organic Letters. ,vol. 5, pp. 535- 537 ,(2003) , 10.1021/OL027447S