The structure of roemrefine

Some Unusual Pavine and Isopavine Alkaloids from Roemeria refracta

“…The mass spectrum of (-)-eschscholtzinone [5] reinforced our belief that we were indeed dealing with a ketonic species. The molecular ion, mlz 337, was also the base peak, but loss of CO from the molecular ion gave rise to an [M -28]+ ion, mlz 309 (32%).…”

“…groups (4)(5)(6)(7)(8), had supplied four isopavines, namely (-)-reframidine [1], (-)-reframine, (-)-reframoline [4], and ( -)-remrefine, together with a variety of proaporphines, aporphines, and other isoquinoline-type bases. Of the aforementioned four isopavines, we were able to reisolate the first three, (-)-reframidine [!…”

“…Of greater interest, however, is the fact that we also obtained two new isopavines and one pavine. The first isopavine, (-)-norreframidine {2], is the only N-nor isopavine base recognized to occur naturally; while the second isopavine, (-)-refractamine [3], is structurally isomeric with the known ( -)-reframoline [4], Our new pavine, (-)-eschscholtzinone [5], is the first known ketonic pavinoid.…”

“…NaBH4 reduction of (-)-eschscholtzinone [5] proceeded in stereospecific fashion to afford (-)-eschscholtzinol [6], C19H17N05, X molecular ion at mlz 339 There was also an ion at mlz 321 formed by loss of H20 from the molecular ion. The base peak, mlz 188, represented the 6,7-methylenedioxy-Nmethoisoquinolinium cation.…”

The Pavine and Isopavine Alkaloids

“…-305°(c=0.2, MeOH) (30) MeO"" MP: (CD 241-242°( EtOH-acetone) (72) ( ) 244-245°( H2G-MeOH) (72) hi --Pv. (CD -147°(c= 1.039, H20) (72) T 1 [a]21D: (CD -188°±3°(c=0.33, H20) (70) MeCrk^J JsDMe…”