Portal de Periódicos da CAPES

Stereoselective Total Synthesis of Enantiomerically Pure 1-Trifluoromethyl Tetrahydroisoquinoline Alkaloids

1998; Wiley; Volume: 1998; Issue: 3 Linguagem: Inglês

10.1002/(sici)1099-0690(199803)1998

1434-193X

Pierfrancesco Bravo, Marcello Crucianelli, Alessandra Farina, Stefano V. Meille, Alessandro Volonterio, Matteo Zanda,

Chemical synthesis and alkaloids

European Journal of Organic ChemistryVolume 1998, Issue 3 p. 435-440 Full Paper Stereoselective Total Synthesis of Enantiomerically Pure 1-Trifluoromethyl Tetrahydroisoquinoline Alkaloids Pierfrancesco Bravo, Pierfrancesco Bravo bravo@dept.chem.polimi.it Search for more papers by this authorMarcello Crucianelli, Marcello Crucianelli C.N.R. − Centro di Studio per le Sostanze Organiche Naturali, Dipartimento di Chimica del Politecnico di Milano, Via Mancinelli 7, I-20131 Milano, Fax: (internat.) +39 (0)2/2399-3080Search for more papers by this authorAlessandra Farina, Alessandra Farina C.N.R. − Centro di Studio per le Sostanze Organiche Naturali, Dipartimento di Chimica del Politecnico di Milano, Via Mancinelli 7, I-20131 Milano, Fax: (internat.) +39 (0)2/2399-3080Search for more papers by this authorStefano Valdo Meille, Stefano Valdo Meille C.N.R. − Centro di Studio per le Sostanze Organiche Naturali, Dipartimento di Chimica del Politecnico di Milano, Via Mancinelli 7, I-20131 Milano, Fax: (internat.) +39 (0)2/2399-3080Search for more papers by this authorAlessandro Volonterio, Alessandro Volonterio C.N.R. − Centro di Studio per le Sostanze Organiche Naturali, Dipartimento di Chimica del Politecnico di Milano, Via Mancinelli 7, I-20131 Milano, Fax: (internat.) +39 (0)2/2399-3080Search for more papers by this authorMatteo Zanda, Matteo Zanda C.N.R. − Centro di Studio per le Sostanze Organiche Naturali, Dipartimento di Chimica del Politecnico di Milano, Via Mancinelli 7, I-20131 Milano, Fax: (internat.) +39 (0)2/2399-3080Search for more papers by this author Pierfrancesco Bravo, Pierfrancesco Bravo bravo@dept.chem.polimi.it Search for more papers by this authorMarcello Crucianelli, Marcello Crucianelli C.N.R. − Centro di Studio per le Sostanze Organiche Naturali, Dipartimento di Chimica del Politecnico di Milano, Via Mancinelli 7, I-20131 Milano, Fax: (internat.) +39 (0)2/2399-3080Search for more papers by this authorAlessandra Farina, Alessandra Farina C.N.R. − Centro di Studio per le Sostanze Organiche Naturali, Dipartimento di Chimica del Politecnico di Milano, Via Mancinelli 7, I-20131 Milano, Fax: (internat.) +39 (0)2/2399-3080Search for more papers by this authorStefano Valdo Meille, Stefano Valdo Meille C.N.R. − Centro di Studio per le Sostanze Organiche Naturali, Dipartimento di Chimica del Politecnico di Milano, Via Mancinelli 7, I-20131 Milano, Fax: (internat.) +39 (0)2/2399-3080Search for more papers by this authorAlessandro Volonterio, Alessandro Volonterio C.N.R. − Centro di Studio per le Sostanze Organiche Naturali, Dipartimento di Chimica del Politecnico di Milano, Via Mancinelli 7, I-20131 Milano, Fax: (internat.) +39 (0)2/2399-3080Search for more papers by this authorMatteo Zanda, Matteo Zanda C.N.R. − Centro di Studio per le Sostanze Organiche Naturali, Dipartimento di Chimica del Politecnico di Milano, Via Mancinelli 7, I-20131 Milano, Fax: (internat.) +39 (0)2/2399-3080Search for more papers by this author First published: March 1998 https://doi.org/10.1002/(SICI)1099-0690(199803)1998:3 3.0.CO;2-2Citations: 35AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat Abstract Enantiomerically pure 1-trifluoromethyl-tetrahydroisoquinoline alkaloid analogues, in which C-1 is a quaternary stereogenic centre, have been synthesized by stereoselective intramolecular Pictet-Spengler reaction of the N-arylethyl γ-trifluoro-β-iminosulfoxide (R)-3, and subsequent elaborations of the sulfinyl auxiliary. The absolute stereochemistry of the stereogenic centre was determined by X-ray diffraction on the α-phenylpropionic ester (1R,2′S)-10. Citing Literature Volume1998, Issue3March 1998Pages 435-440 RelatedInformation