CONFIGURATIONAL ANALYSIS OF RHYNCHOPHYLLINE-TYPE OXINDOLE ALKALOIDS - ABSOLUTE CONFIGURATION OF CILIAPHYLLINE RHYNCHOCILINE SPECIONOXEINE ISOSPECIONOXEINE ROTUNDIFOLINE AND ISOROTUNDIFOLINE

From a general configurational and conformational analysis of rhynchophyllinoid alkaloids, unique physical criteria are developed that differentiate between the 8 possible configurational types. The criteria are applied to 6 rhynchophylline-type alkaloids of unknown configurations and show that ciliaphylline, specionoxeine and isorotundifoline have the normal B configuration while rhynchociline, isospecionoxeine and rotundifoline have the normal A configuration. All 6 alkaloids have the C15Hα absolute stereochemistry. © 1968.