STEREOSELECTIVE TOTAL SYNTHESIS OF ENANTIOMERICALLY PURE 1-TRIFLUOROMETHYL TETRAHYDROISOQUINOLINE ALKALOIDS

Authors
BRAVO P CRUCIANELLI M FARINA A MEILLE SV VOLONTERIO A ZANDA M
Citation
P. Bravo et al., STEREOSELECTIVE TOTAL SYNTHESIS OF ENANTIOMERICALLY PURE 1-TRIFLUOROMETHYL TETRAHYDROISOQUINOLINE ALKALOIDS, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (3), 1998, pp. 435-440
Citations number
55
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY → ACNP
ISSN journal
1434193X
Issue
3
Year of publication
1998
Pages
435 - 440
Database
ISI
SICI code
1434-193X(1998):3<435:STSOEP>2.0.ZU;2-4
Abstract
Enantiomerically pure 1-trifluoromethyl-tetrahydroisoquinoline alkaloi d analogues, in which C-1 is a quaternary stereogenic centre, have bee n synthesized by stereoselective intramolecular Pictet-Spengler reacti on of the N-arylethyl gamma-trifluoro-beta-iminosulfoxide (R)-3, and s ubsequent elaborations of the sulfinyl auxiliary. The absolute stereoc hemistry of the stereogenic centre was determined by X-ray diffraction on the alpha-phenylpropionic ester (1R,2'S)-10.