Palladium(0)-catalyzed [2 + 2 + 1] cyclization of 1,6-enynes with vinyl bromides: a highly diastereoselective synthesis of tetrahydro-1H-cyclopenta[c]furans bearing two quaternary carbon centers

作者: Yunxia Diao , Zhijun Zuo , Hui Wang , Jingjing Liu , Xinjun Luan

DOI: 10.1039/C7OB00768J

关键词: CatalysisMedicinal chemistryPalladiumQuaternary carbonChemistryOrganic chemistry

摘要: A new cascade process has been accomplished for the synthesis of tetrahydro-1H-cyclopenta[c]furans through palladium-catalyzed [2 + 2 1] cyclization 1,6-enynes with vinyl bromides. Notably, key feature this transformation is use bromides as C1 building block. Various functionalized bearing two quaternary carbon centers could be obtained in good yields excellent diastereoselectivities.

参考文章(69)
Yu-Qi Wang, Yu-Tao He, Lu-Lu Zhang, Xin-Xing Wu, Xue-Yuan Liu, Yong-Min Liang, Palladium-Catalyzed Radical Cascade Iododifluoromethylation/Cyclization of 1,6-Enynes with Ethyl Difluoroiodoacetate. Organic Letters. ,vol. 17, pp. 4280- 4283 ,(2015) , 10.1021/ACS.ORGLETT.5B02068
Barry M. Trost, Jacques Dumas, New stragegy for the total synthesis of 1.alpha.-hydroxyvitamin D derivatives Journal of the American Chemical Society. ,vol. 114, pp. 1924- 1925 ,(1992) , 10.1021/JA00031A082
Corinne Aubert, Olivier Buisine, Max Malacria, The behavior of 1,n-enynes in the presence of transition metals. Chemical Reviews. ,vol. 102, pp. 813- 834 ,(2002) , 10.1021/CR980054F
Nobuyasu Enoki, Akio Furusaki, Katsunao Suehiro, Ryoichi Ishida, Takeshi Matsumoto, Epoxydictymene, a new diterpene from the brown alga Tetrahedron Letters. ,vol. 24, pp. 4341- 4342 ,(1983) , 10.1016/S0040-4039(00)88336-7
Mathias Schelwies, Adrian L. Dempwolff, Frank Rominger, Günter Helmchen, Gold-catalyzed intermolecular addition of carbonyl compounds to 1,6-enynes. Angewandte Chemie. ,vol. 46, pp. 5598- 5601 ,(2007) , 10.1002/ANIE.200701378
Jae-Hyuk Jang, Yukihiro Asami, Jun-Pil Jang, Sun-Ok Kim, Dong Oh Moon, Kee-Sun Shin, Daisuke Hashizume, Makoto Muroi, Tamio Saito, Hyuncheol Oh, Bo Yeon Kim, Hiroyuki Osada, Jong Seog Ahn, Fusarisetin A, an Acinar Morphogenesis Inhibitor from a Soil Fungus, Fusarium sp. FN080326 Journal of the American Chemical Society. ,vol. 133, pp. 6865- 6867 ,(2011) , 10.1021/JA1110688
Eun Joo Kang, Eun Lee, Total Synthesis of Oxacyclic Macrodiolide Natural Products Chemical Reviews. ,vol. 105, pp. 4348- 4378 ,(2005) , 10.1021/CR040629A
Angela Marinetti, Hélène Jullien, Arnaud Voituriez, Enantioselective, transition metal catalyzed cycloisomerizations. Chemical Society Reviews. ,vol. 41, pp. 4884- 4908 ,(2012) , 10.1039/C2CS35020C
Alberto Arnone, Adriana Bava, Giovanni Fronza, Luciana Malpezzi, Gianluca Nasini, Microbial transformations of the taxan ring of 10-DAB by some strains of the fungus Curvularia lunata: formation of the bis-abeotaxanes wallifoliol and 4-deacylwallifoliol. Journal of Natural Products. ,vol. 73, pp. 1049- 1052 ,(2010) , 10.1021/NP900765Y
Jie Li, Liang Xu, Feng-Peng Wang, New cytotoxic myrsinane-type diterpenes from Euphorbia prolifera. Helvetica Chimica Acta. ,vol. 93, pp. 746- 752 ,(2010) , 10.1002/HLCA.200900288