caa a22 4500 445878223 CHVBK 20180317145534.0 cr unu---uuuuu 170323e20110201xx s 000 0 eng 10.1007/s11030-010-9255-4 doi (NATIONALLICENCE)springer-10.1007/s11030-010-9255-4 Parallel synthesis of natural product-like polyhydroxylated pyrrolidine and piperidine alkaloids [Elektronische Daten] [Yi-Fan Chang, Chih-Wei Guo, Ting-Hao Chan, Yi-Wen Pan, En-Lun Tsou, Wei-Chieh Cheng] The preparation of natural product-like polyhydroxylated pyrrolidine and piperidine alkaloids using a combination of solid- and solution-phase organic synthesis is described. The key intermediates, enantiopure five- or six-membered tri-O-benzyl cyclic nitrones, were efficiently prepared on solid support from accessible chiral furanosides and pyranosides, respectively. The substituent diversity was achieved by a diastereoselective addition of a variety of Grignard reagents to the cyclic nitrones in solution-phase synthesis. All reaction steps and work-up procedures were modified to allow the use of automated equipment. A 36-membered demonstration library with three diversity elements (core, configuration, and substituent) was prepared in good yield and purity. Springer Science+Business Media B.V., 2010 Natural Product-like library nationallicence Solid-phase organic synthesis nationallicence Alkaloids nationallicence Substituent diversity nationallicence Core diversity nationallicence Stereogenic diversity nationallicence Privileged scaffolds nationallicence Chang Yi-Fan The Genomics Research Center, Academia Sinica, No. 128, Academia Road Sec. 2, Nankang District, 11529, Taipei, Taiwan, ROC aut Guo Chih-Wei The Genomics Research Center, Academia Sinica, No. 128, Academia Road Sec. 2, Nankang District, 11529, Taipei, Taiwan, ROC aut Chan Ting-Hao The Genomics Research Center, Academia Sinica, No. 128, Academia Road Sec. 2, Nankang District, 11529, Taipei, Taiwan, ROC aut Pan Yi-Wen The Genomics Research Center, Academia Sinica, No. 128, Academia Road Sec. 2, Nankang District, 11529, Taipei, Taiwan, ROC aut Tsou En-Lun The Genomics Research Center, Academia Sinica, No. 128, Academia Road Sec. 2, Nankang District, 11529, Taipei, Taiwan, ROC aut Cheng Wei-Chieh The Genomics Research Center, Academia Sinica, No. 128, Academia Road Sec. 2, Nankang District, 11529, Taipei, Taiwan, ROC aut Molecular Diversity Springer Netherlands 15/1(2011-02-01), 203-214 1381-1991 15:1<203 2011 15 11030 https://doi.org/10.1007/s11030-010-9255-4 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s11030-010-9255-4 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Chang Yi-Fan The Genomics Research Center, Academia Sinica, No. 128, Academia Road Sec. 2, Nankang District, 11529, Taipei, Taiwan, ROC aut NATIONALLICENCE 700 1- Guo Chih-Wei The Genomics Research Center, Academia Sinica, No. 128, Academia Road Sec. 2, Nankang District, 11529, Taipei, Taiwan, ROC aut NATIONALLICENCE 700 1- Chan Ting-Hao The Genomics Research Center, Academia Sinica, No. 128, Academia Road Sec. 2, Nankang District, 11529, Taipei, Taiwan, ROC aut NATIONALLICENCE 700 1- Pan Yi-Wen The Genomics Research Center, Academia Sinica, No. 128, Academia Road Sec. 2, Nankang District, 11529, Taipei, Taiwan, ROC aut NATIONALLICENCE 700 1- Tsou En-Lun The Genomics Research Center, Academia Sinica, No. 128, Academia Road Sec. 2, Nankang District, 11529, Taipei, Taiwan, ROC aut NATIONALLICENCE 700 1- Cheng Wei-Chieh The Genomics Research Center, Academia Sinica, No. 128, Academia Road Sec. 2, Nankang District, 11529, Taipei, Taiwan, ROC aut NATIONALLICENCE 773 0- Molecular Diversity Springer Netherlands 15/1(2011-02-01), 203-214 1381-1991 15:1<203 2011 15 11030 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer