Synthesis of unsubstituted 5 chi-cholesteno(3,2-d)- (5), (2,3-d)- (12)
, (3,4-d)- (15) and 5 <-- and 5 beta-cholest-3-eno(4,3-d) pyrimidines
(21) and (21') has been achieved using hydroxymethylene derivatives of
relevant cholestanones prepared from cholesterol(1). Their 2'-derivat
ives (5a - 5e), (12a), (15a - 15c), (21a - 21c) and (21'a,21'b) could
also be prepared. Attempts to prepare cholest-1-eno(1,2-d) pyrimidine
system through 5 chi-cholestan-1-one(28) failed. 5 chi-Cholest-6-eno(7
,6-d)pyrimidine(33) was prepared by the reaction of cholestan-7-one wi
th trisformylaminomethane. Three Cotton effects were observed between
350-200 nm in all these compounds in their CD spectra. They have been
assigned to n --> pi and pi --> pi* transitions from long to short wa
ve lengths. Quadrant rule has been applied for determining the sign of
the first band CD, while helicity rule has been applied for the third
band CD.