Y. Oka, M. Motohashi, H. Sugihara
Apr 25, 1977
Citations
0
Influential Citations
11
Citations
Journal
Chemical & Pharmaceutical Bulletin
Abstract
2-Amino-5, 6-dihydroxy-1, 2, 3, 4-tetrahydro-1-naphthalenol (1), 5, 6-dihydroxy-2-methylamino-1, 2, 3, 4-tetrahydro-1-naphthalenol (2) and 5, 6-dihydroxy-2-isopropylamino-1, 2, 3, 4-tetrahydro-1-naphthalenol (3), which are conformationally rigid derivatives of noradrenaline, adrenaline and isoproterenol respectively, were synthesized from 2-amino-5, 6-dimethoxy-3, 4-dihydro-1 (2H)-naphthalenone (15) prepared by several modifications of the known procedures. The reduction of 1-carbonyl group into hydroxy group at the final step of the syntheses showed unsatisfactory stereoselectivity affording mixtures of 1, 2-cis and 1, 2-trans derivatives. Each cis and trans isomer of 2 (2-cis and 2-trans) was obtained by a sequence of reactions employing 5, 6-dibenzyloxy materials via cis-and trans-2-(N-benzyl-N-methylamino)-5, 6-dibenzyloxy-1, 2, 3, 4-tetrahydro-1-naphthalenol (26-cis and 26-trans).