Alkaloids ofThalictrum collinum

Abstract

The plant ~alictrum collinum Wallr. family Ranunculaceae has been little studied chemi

β-Phenylethylamines and the isoquinoline alkaloids (July 1998 to June 1999)

“…21 (±)-Coreximine 13 has been synthesised from hydrastinine 11 as described in section 2, and a similar synthesis of (±)-corydalisol 77 has also been achieved. 110 10 Protopines Alkaloids of the protopine group have been isolated from the following plant species: Fumaria agraria 92 cryptopine and protopine Fumaria bastardii 20 protopine Fumaria capreolate 92 cryptopine and protopine Fumaria densiflora 92 cryptopine Fumaria muralis 92 protopine Fumaria officinalis 92 protopine Fumaria parviflora 92 cryptopine and protopine Fumaria vaillantii 92 cryptopine and protopine Hypercoum leptocarpum 21 protopine Thalictrum triternatum 111 allocryptopine and protopine. X-Ray crystallographic studies of a and b-allocryptopine confirm that these are polymorphic forms of the same substance.…”

“…Aporphine alkaloids have been isolated from the following plant species, the five marked with asterisks being new alkaloids: Annona cherimola 17 norisocorydine, norstephalgine and romucosine Annona purpurea 130 lirindine, N-methyllaurotetanine, norpurpureine, thalicmidine, 7-hydroxydehydrothalicsimidine* 117a and N-formyl-7-hydroxydehydronorthalicsimidine* 117b Anomianthus dulcis 1 anonaine, anolobine, asimilobine, isoboldine, N-methyllaurotetanine, nornuciferine and roemerine Berberis vulgaris 19 magnoflorine Cassytha filiformis 131 actinodaphnine, N-methylactinodaphnine, cassythicine, cathafiline, cathaformine, ocoteine, and predicentrine Croton hemiargyreus 89 glaucine Fissistigma balansae 132 fissilandione* 118a and norfissilandione* 118b Glaucium fimbrilligerum 133 bulbocapnine b-N-oxide* 119 Elastostema sinuata 134 procoteine, thalicsimidine, thaliporphine and wilsonirine Thalictrum przewalskii 22 magnoflorine and N-methylnantenine Thalictrum triternatum 111 glaucine, thalfine and thalmine…”

β-Phenylethylamines and the isoquinoline alkaloids

“…Oxidation of cularidine with lead tetra-acetate afforded a 2: 3 mixture of limousamine (61) and its C-4 epimer. 0-Methylation and further oxidation with 2,3-dichloro-5,6-dicyanobenzoquinone then afforded dioxocularine (62 ; R' = H, R2 = OMe).lo6 Oxidation of the diphenol (63) with potassium ferricyanide yielded a mixture of sarcocapnidine (64; R' = OH, R2 = H, R3 = Me) and enneaphylline (64; R' = H, R2 = OH, R3 = Me), but oxidation of the N-borane complex of (63) with the 2,3,10,11,12-~ubstituted base (76; R = OH), which on treatment with diethyl chlorophosphate followed by reduction with sodium in liquid ammonia gave the pseudoberberine (76; R = H). The process must involve oxidative fission of the 8-8a bond and re-cyclization between C-8 and the original C-12.…”