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Stereoselective Total Synthesis of Enantiomerically Pure 1-Trifluoromethyl Tetrahydroisoquinoline Alkaloids

✍ Scribed by Pierfrancesco Bravo; Marcello Crucianelli; Alessandra Farina; Stefano Valdo Meille; Alessandro Volonterio; Matteo Zanda

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 474 KB
Volume: 1998
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199803)1998:3<435::aid-ejoc435>3.0.co;2-2

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✦ Synopsis

Enantiomerically pure 1-trifluoromethyl-tetrahydroisoquino-fluoro-β-iminosulfoxide (R)-3, and subsequent elaborations of the sulfinyl auxiliary. The absolute stereochemistry of the line alkaloid analogues, in which C-1 is a quaternary stereogenic centre, have been synthesized by stereoselective intra-stereogenic centre was determined by X-ray diffraction on the α-phenylpropionic ester (1R,2ЈS)-10. molecular Pictet-Spengler reaction of the N-arylethyl γ-tri-

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