56178-05-3Relevant academic research and scientific papers
5,10b-Ethanophenanthridine amaryllidaceae alkaloids inspire the discovery of novel bicyclic ring systems with activity against drug resistant cancer cells
Henry, Sean,Kidner, Ria,Reisenauer, Mary R.,Magedov, Igor V.,Kiss, Robert,Mathieu, Véronique,Lefranc, Florence,Dasari, Ramesh,Evidente, Antonio,Yu, Xiaojie,Ma, Xiuye,Pertsemlidis, Alexander,Cencic, Regina,Pelletier, Jerry,Cavazos, David A.,Brenner, Andrew J.,Aksenov, Alexander V.,Rogelj, Snezna,Kornienko, Alexander,Frolova, Liliya V.
, p. 313 - 328 (2016)
Plants of the Amaryllidaceae family produce a large variety of alkaloids and non-basic secondary metabolites, many of which are investigated for their promising anticancer activities. Of these, crinine-type alkaloids based on the 5,10b-ethanophenanthridin
Synthesis of Amaryllidaceae alkaloids, siculine, oxocrinine, epicrinine, and buflavine
Kodama, Sumiaki,Takita, Hirofumi,Kajimoto, Tetsuya,Nishide, Kiyoharu,Node, Manabu
, p. 4901 - 4907 (2007/10/03)
Three crinane type of alkaloids isolated from Amaryllidaceae family were synthesized by taking advantage of the PIFA-mediated intramolecular p-p′ diphenol coupling reaction of norbelladine derivatives. Furthermore, buflavine was also prepared by using the p-p′ diphenol coupling followed by dienone-phenol rearrangement as a key step.
An oxidative intramolecular phenolic coupling reaction for the synthesis of amaryllidaceae alkaloids using a hypervalent iodine(III) reagent
Kita, Yasuyuki,Takada, Takeshi,Gyoten, Michiyo,Tohma, Hirofumi,Zenk, Meinhart H.,Eichhorn, Joerg
, p. 5857 - 5864 (2007/10/03)
The oxidative intramolecular phenolic coupling reaction of norbelladine derivatives (1) was investigated with the aim of preparing amaryllidaceae alkaloids. Spirodienone compounds (2), which are intermediates for the synthesis of an amaryllidaceae alkaloid, (+)-maritidine, or phenol ether derivatives containing the 5,6,7,8-tetrahydrobenzazocine systems (9), were selectively obtained by the reaction of 1 and the hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA). Both p-p′ coupling (11) and p-o′ coupling spirodienone compounds (12) were obtained by the reaction of phenol derivatives having an alkoxy group at the C-3′ position (10) with PIFA.
