88199-28-4

Upstream product

• 6874-98-2 16-epi-vellosimine 
• 2520-44-7 (2S,6S,13S)-3-Eth-(E)-ylidene-13-formyl-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizine-13-carboxylic acid methyl ester 
• 2520-44-7 (+)-polyneuridine aldehyde 
• 639-36-1 E-akuammidine 
• 124016-70-2 C₂₆H₃₄N₂O₆ 
• 124020-58-2 C₂₆H₃₆N₂O₆ 
• 124016-71-3 (2R,6S,8R,13aR)-3-Eth-(Z)-ylidene-8-(2-methoxy-ethoxymethoxy)-13-methyl-1,3,4,7,8,13,13a,13b-octahydro-2H,6H-2,7-cyclo-6,8a-methano-pyrido[1',2':1,2]azepino[3,4-b]indole 
• 137032-24-7 C₂₄H₃₄N₂O₄ 
• 509-38-6 (2R,6S,8R,13aR)-3-Eth-(Z)-ylidene-13-methyl-1,3,4,7,8,13,13a,13b-octahydro-2H,6H-2,7-cyclo-6,8a-methano-pyrido[1',2':1,2]azepino[3,4-b]indol-8-ol 
• 124020-57-1 C₃₂H₅₀N₂O₆Si 
• 124020-55-9 C₂₆H₃₅BrN₂O₆ 
• 124016-69-9 C₂₆H₃₆N₂O₆ 
• 137032-22-5 C₂₄H₃₄N₄O₃ 
• 137120-65-1 C₂₂H₂₈N₂O₄ 

Downstream Products

• 604-99-9 10-deoxysarpagine 
• 482-68-8 Sarpagine 
• 604-99-9 10-de oxy-sarpagine 
• 34020-07-0 vinorine 
• 6874-98-2 (+)-vellosimine 
• 604-99-9 16-epi-Koumidine 
• 6874-98-2 (+)-3-ethylidene-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methanoindolo[2,3-a]quinolizine-13-carboxaldehyde 

Relevant academic research and scientific papers

Polyneuridine Aldehyde Esterase: an Unusually Specific Enzyme involved in the Biosynthesis of Sarpagine Type Alkaloids

Polyneuridine aldehyde esterase is a highly substrate specific enzyme which catalyses the conversion of the monoterpenoid C10-unit into C9-unit at the stage of polyneuridine aldehyde in the biosynthesis of sarpagine type alkaloids.

Enantioselective, protecting-group-free total synthesis of sarpagine alkaloids-A generalized approach

A generalized synthetic access to sarpagine alkaloids through a joint synthetic sequence has been accomplished. Its applicability is showcased by the enantioselective total syntheses of vellosimine (1), N-methylvellosimine (3 ), and 10-methoxyvellosimine (8). The synthetic sequence is concise (eight steps) from known compound 13, and requires no protecting groups. The indole heterocycle was introduced in the last step. This strategy allows access to sarpagine alkaloids through a shared synthetic route leading to precursor 10, which we term "privileged intermediate". Starting from this intermediate, all sarpagine alkaloids can be synthesized using phenylhydrazines with different substitution patterns (15-17). Our approach brings about the advantage, that synthesis optimization only needs to be performed once for many natural products. The key features of the synthesis are a [5+2]-cycloaddition and a ring enlargement.

Stereoselective Transformation of Ajmaline into Three Minor Gelsemium Alkaloids, Koumidine, (19Z)-Anhydrovobasinediol and N-Demethoxyrankinidine and their Absolute Configuration

Ajmaline was converted into new Gelsemium alkaloids, 19Z-anhydrovobasinediol and N-demethoxyrankinidine, via koumidine along the biomimetic sequence, and the absolute configuration of these alkaloids was determined by these transformations.

Studies on Apocynaceae: Hemi-Synthesis of Vellosimine from Rhazine - Application of HOMCOR (COSY)-2D NMR Spectroscopy in Structure Eludication of Ajmaline-Sarpagine Skeleton

The rare indole alkaloid vellosimine (1) has been isolated from Rauwolfia reflexa Teism and Binn.The occurrence of this indolic base has been observed for the first time in R. reflexa.The hemi-synthesis of this compound from rhazine has been achieved.The study of the HOMCOR (COSY)-2D NMR spectroscopy of vellosimine provides important information on structure of the alkaloids having ajmaline-sarpagine skeleton.

Biogenetic link between sarpagine and ajmaline type alkaloids

A new enzyme - vinocrine synthase - isolated from cell suspension cultures of Rauwolfia serpentina, links sarpagine and ajmaline alkaloids by catalyzing the acetyl-coenzyme-A dependent biosynthesis of the ajmalan skeleton from sarpagan type compounds.