77513-46-3Relevant articles and documents
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.
Biomimetic synthesis of Nauclea indole alkaloids, naucleidinal, and 3- epi-naucleidinal, by stereoselective rearrangement of strictosamide and the vincoside lactam aglycones
Takayama, Hiromitsu,Miyabe, Yuhko,Shito, Toshiaki,Kitajima, Mariko,Aimi, Norio
, p. 2192 - 2194 (2007/10/03)
Based on a biogenetic consideration, a Nauclea alkaloid, naucleidinal (6), and its 3-epimer (7) were stereoselectively prepared from the aglycones of strictosamide and the vincoside lactam, and their absolute stereochemistry was confirmed.
