Vincamajinine — A new alkaloid fromVinca major

A General Strategy for the Synthesis of Vincamajine-Related Indole Alkaloids: Stereocontrolled Total Synthesis of (+)-Dehydrovoachalotine, (−)-Vincamajinine, and (−)-11-Methoxy-17-epivincamajine as Well as the Related Quebrachidine Diol, Vincamajine Diol, and Vincarinol1

“…(+)-Quebrachidine ( 3 ), reported to show psychosedative and adrenergic activity, was first isolated in 1963 from the extract of the basified ground leaves of Aspidosperma quebracho-blanco and later from many other species. , The related (−)-vincamajine ( 4 ), an N a -methyl analogue of (+)-quebrachidine, has also been obtained from many species. 12e,g,j,l, Both (−)-11-methoxyvincamajine ( 5 ) 9b and 10-methoxyvincamajine ( 6 ) 12d, have only been isolated from Alstonia species. The isolation of (−)-vincamajinine ( 7 , 17-epivincamajine) from the aerial parts of Vinca major was reported by Zhukovich and Vachnadze in 1985 . (+)-Vincarine ( 8 ), an N a -H analogue of (−)-vincamajinine, was isolated from Vinca erecta , Vinca herbacea , and Vinca major .…”

“…(+)-Vincarine ( 8 ), an N a -H analogue of (−)-vincamajinine, was isolated from Vinca erecta , Vinca herbacea , and Vinca major . The constitution and relative configuration of these indole alkaloids were determined on the basis of NMR studies and chemical correlation or confirmed by chemical conversion and spectral data. − These indole alkaloids typically possess a unique rigid, caged hexacyclic carbon skeleton which contains seven stereogenic centers (carbons 2, 3, 5, 7, 15, 16, and 17) as well as the key olefinic bond at C(19)−C(20) in the E -configuration. However, the configuration of the C(17)-hydroxyl group in 3 − 6 [17( S )] is different from that in 7 − 9 [17( R )].…”

Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

“…Two new tryptamine-related alkaloids, psychotrimine (167) and psychopentamine (168), were isolated from the leaves of Psychotria rostrata. 94 Chimonanthidine (169) was isolated from the seeds of Chimonanthus praecox, and this structure, including the absolute configuration, was elucidated by spectroscopic analyses and total synthesis from the tryptamine derivative (170) (Scheme 31).…”