56519-07-4Relevant academic research and scientific papers
Main glucosidase conversion products of the gluco-alkaloids dolichantoside and palicoside
Brandt, Viviane,Tits, Monique,Penelle, Jacques,Frederich, Michel,Angenot, Luc
, p. 653 - 659 (2001)
The enzymatic glucose cleavage of palicoside revealed the biosynthetic pathway to akagerine, whereas the conversion of dolichantoside led to a new quaternary heteroyohimbine alkaloid named Nb-methyl-21-β-hydroxy-mayumbine. The hypothetical models of reactions occurring after the conversion of both substrates are proposed. Dolichantoside and palicoside, as well as Strychnos mellodora stem bark crude ethanol extract, exhibit significant antimycotic activity against human pathogens in presence of specific glucosidase.
Bioinspired Transformations Using Strictosidine Aglycones: Divergent Total Syntheses of Monoterpenoid Indole Alkaloids in the Early Stage of Biosynthesis
Sakamoto, Jukiya,Ishikawa, Hayato
, (2021/12/24)
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.
First Enantioselective Synthesis of (-)-Akagerine by a Chemoenzymatic Approach
Danieli, Bruno,Lesma, Giordano,Mauro, Marina,Palmisano, Giovanni,Passarella, Daniele
, p. 2506 - 2513 (2007/10/02)
(-)-Akagerine (1) was synthesized in an efficient and stereocontrolled fashion from the readily available (1S,2R)-cyclohexenedimethanol monoacetate 4.Key steps were the cleavage of the C(17)/C(18) bond of a 14a and the regio- and stereoselective cyclizati
