Alkaloid studies LI. The structure of aspidodasycarpine.

✍ Scribed by M. Ohashi; J.A. Joule; Carl Djerassi

• Publisher: Elsevier Science
• Year: 1964
• Tongue: French
• Weight: 288 KB
• Volume: 5
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)93313-1

✦ Synopsis

The Bmzilian tree Aspidosperma dasycarpon 3 A. DC. has already yielded a number of interesting congeners4 (II-VI) of I u eine (I$ as well as the novel alkaloid apparicine (Vll).6 We should now like to record the isolation of still another alkaloid, "aspidodasycarpine, " to which we attribute structure VIII. Such a skeleton has not been hitherto encountered among Aspidosperma olkoloids. qQ VII m* l;-,: /; A R IV0 H V<iH CH3 vl (HCH bH CH3 2 Aspidodasycarpine exhibited m.p. 207-209O, [a], -101' (all rotations in CHC13), hEAt; 240 and 297 rqs (log l 3.96 and 3.63-typical of dihydroindole), A$:'3 2.90 (m), 5.76 (s) and 6.25 (m) p and ik empirical formula was shown by mass spectrometry and elementary analysis to correspond to C21H26N204. The unsubstituted nature of the four oromotic positions was demonstrated by the n.m.r.