The configuration of venoterpine

Tetrahedron Letters
1985.0

Abstract

Venoterpine and cantleyine were chemically correlated and shown to have the same absolute configuration. Venoterpine 1' and cantleyine z2 are monoterpene alkaloids of wide natural distribution? The structure of z was proved by a chemical correlation with loganin' but the absolute configuration of 1 so far rests only a CD study4. Until now it was generally believed albeit without explanation that venoterpine 1 had the opposite configurationfromthatof cantleyine2. This situation has recently been questioned' and the simultaneous isolation in our laboratory of 1 and _2. in the same plants lead us to reexamine the situation. Compounds 1 and 2 were isolated from AZstonia angustiZoba, A.pnewnatophora and A.spatu-Zata6. Their gross structureswere established by comparison of their physical propertied_iith literaturedataTf2. Examination of their 13 C NMR spectra disclosed a similar substitution pattern for their cyclopentane ring (Table I). All these data confirmed the known relative configuration of 1 and 2, the absolute configuration of 1 only remaining to be determined-This was established by a chemical correlation between 2 and 1 based on the flash pyrolysis of the carboxylic acid derived from cantleyine. Barium hydroxide hydrolysis of z ((aID=-4@";CHCl3) followed by CO2 neutralization yielded an acid, which was dissolved in THF (2mg/ml) and submitted to vacuum flash pyrolysis in a vertical hot tube (glass beads fillinq) preheated to 460°C. Condensation of the eluate yielded tars and a single non-polar compound inall respects identical to venoterpine (MS, IR, NMR, UV, TLC). The optical rotation of this material ((a]D=+38";CHCl3) was identical to the value found for natural 1 ClalD=+32";CHC13) within experimental error. We thus conclude that 1 and 2 have the same absolute configuration as Loganin, which is probably their common genitor.

Knowledge Graph

Similar Paper