Dw. Oliver et al., STEREOCHEMISTRY OF 4-AMINO-(D-3)-TRISHOMOCUBANES - NMR-STUDY OF 3-PHENYL-4-AMINO-(D-3)-TRISHOMOCUBANE, Magnetic resonance in chemistry, 32(6), 1994, pp. 330-334
Amino compounds of the highly symmetrical (D-3)-trishomocubane were re
cently shown to possess promising biological activities, i.e. antiviri
al and antiparkinson. This series was synthesized via a modified Ritte
r reaction. The unique hydrocarbon skeleton of these compounds has a D
-3 point group symmetry with a propeller shape. Several geometrical is
omers are possible for the derivatives of (D-3)-trishomocubane, This p
aper reports the complete H-1 and C-13 NMR assignments and the configu
ration at C-4 of one of the most promising compounds of the present se
ries, i.e. 3-phenyl-damino-(D-3)-trishomocubane. The C-13 NMR spectrum
of this amine indicates the presence of only one geometrical isomer f
or the compound. NOE experiments on the fully assigned H-1 NMR spectru
m show that this isomer has the 3S4S/3R4R configuration, and not the 3
S4R/3R4S configuration. These results indicate that the Ritter rearran
gement proceeds stereospecifically and that it provides a facile metho
d for the synthesis of (D-3)-trishomocuban-4-amines from tertiary alco
hols of ntacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecan-8-ol.