50439-68-4

Usage

InChI:InChI=1/C22H28N2O3/c1-4-14-12-24-10-9-16-15-7-5-6-8-19(15)23-21(16)20(24)11-17(14)18(13-26-2)22(25)27-3/h5-8,13-14,17,20,23H,4,9-12H2,1-3H3/b18-13+/t14-,17-,20-/m0/s1

Upstream product

• 18904-54-6 Epiallo-corynanthein 
• 116287-97-9 (-)-secologanin aglucone-O-silyl ether 
• 5027-70-3 17-oxo-corynane-16-carboxylic acid methyl ester 
• 61166-43-6 17,17-dimethoxy-corynane-16-carboxylic acid methyl ester 
• 186581-53-3 diazomethane 
• 77-78-1 dimethyl sulfate 
• 86980-97-4 1,4,6,7,12,12b-Hexahydroindolo<2,3-a>chinolizin-3-carbonsaeure-ethylester 
• 26076-15-3 2-((2R,3S,12bS)-3-Ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl)-3-oxo-propionic acid methyl ester 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 19005-93-7 1H-indol-2-ylcarboxaldehyde 
• 1395097-35-4 C₂₀H₁₉N₃O₆S 
• 1395097-36-5 C₂₇H₂₉N₃O₈S 

Relevant academic research and scientific papers

Bioinspired Transformations Using Strictosidine Aglycones: Divergent Total Syntheses of Monoterpenoid Indole Alkaloids in the Early Stage of Biosynthesis

A series of bioinspired transformations that are applied to convert strictosidine aglycones into monoterpenoid indole alkaloids is reported. The highly reactive key intermediates, strictosidine aglycones, were prepared in situ by simple removal of a silyl protecting group from the silyl ether derivatives, and converted selectively via bioinspired transformations under substrate control into heteroyohimbine- and corynantheine-type, and akagerine and naucleaoral related alkaloids. Thus, concise, divergent total syntheses of 13 monoterpenoid indole alkaloids, (?)-cathenamine, (?)-tetrahydroalstonine, (+)-dihydrocorynantheine, (?)-corynantheidine, (?)-akagerine, (?)-dihydrocycloakagerine, (?)-naucleaoral B, (+)-naucleidinal, (?)-naucleofficines D and III, (?)-nauclefiline, and (?)-naucleamides A and E, were accomplished in fewer than 13 steps.

Total synthesis of (±)-hirsutine: Application of phosphine-catalyzed imine-allene [4 + 2] annulation

The total synthesis of the indole alkaloid hirsutine has been achieved, with a key step being the application of our phosphine-catalyzed [4 + 2] annulation of an imine with ethyl α-methylallenoate. From commercially available indole-2-carboxaldehyde, the target was synthesized in 14 steps and 6.7% overall yield.

Enantioselective syntheses of corynanthe alkaloids by Chiral Br?nsted acid and palladium catalysis

Synergistic catalysis: Three indole alkaloids (-)-corynantheidine, (+)-corynantheine and (+)-dihydro-corynantheine were prepared following a short and common strategy based on the binol phosphoric acid catalyzed enantioselective Pictet-Spengler reaction,

Preparation of (±)-hirsutine and (±)-3-isocorynantheidine

Preparation of indole alkaloids (±)-hirsutine (1) and (±)-3- isocorynantheidine (2) is described.

Stereoselective Total Synthesis of (+/-)-Hirsutine and Related Corynanthe Alkaloids

In a completely stereoselective sequence, an analogue of dihydrosecologanin aglucone has been synthesised via a novel cyclopentenedione dimer and converted into tetracyclic indole alkaloids.