11014-01-0Relevant academic research and scientific papers
Total synthesis of (±)-8-Oxo-erythrinine, (±)-8-oxo-erythraline, and (±)-clivonine
He, Maomao,Qu, Chunrong,Ding, Bingbing,Chen, Hao,Li, Yangyan,Qiu, Guofu,Hu, Xianming,Hong, Xuechuan
, p. 3240 - 3250 (2015)
Total syntheses of the erythrina alkaloids (±)-8-oxo-erythrinine and (±)-8-oxo-erythraline have been developed, based on a substrate-controlled intramolecular 6-exo-trig selective radical spirocyclization that establishes the quaternary center of the B-ri
Total synthesis of the lycorenine-type amaryllidaceae alkaloid (±)-Clivonine via a biomimetic ring-switch from a lycorine-type progenitor
Giro Mannas, Carles,Paddock, Victoria L.,Bochet, Christian G.,Spivey, Alan C.,White, Andrew J. P.,Mann, Inderjit,Oppolzer, Wolfgang
, p. 5176 - 5178 (2010)
A fully diastereoselective total synthesis of the lycorenine-type Amaryllidaceae alkaloid (±)-clivonine (19) is reported via a route that employs for the first time a biomimetic ring-switch from a lycorine-type progenitor, thereby corroborating experimentally the biogenetic hypothesis first expounded for these compounds by Barton in 1960.
Total synthesis of the Amaryllidaceae alkaloid clivonine
Haning, Helmut,Giro-Manas, Carles,Paddock, Victoria L.,Bochet, Christian G.,White, Andrew J. P.,Bernardinelli, Gerald,Mann, Inderjit,Oppolzer, Wolfang,Spivey, Alan C.
experimental part, p. 2809 - 2820 (2011/05/12)
Two syntheses of the Amaryllidaceae alkaloid clivonine (1) are described. Both employ previously reported 7-arylhydrindane 6 as an intermediate but differ in the method employed for subsequent introduction of what becomes the ring-B lactone carbonyl carbon (C7). The synthesis featuring a Bischler-Napieralski reaction for this transformation constitutes the first asymmetric synthesis of natural (+)-clivonine. Crystal structures for compounds (±)-13, (±)-16, (-)-20 and (±)-28 are also reported.
SYNTHESIS OF AN AMARYLLIDACEAE ALKALOID, (+/-)-HIPPEASTRINE
Katakawa, Jun'ichi,Merugi, Haruo,Irie, Hiroshi
, p. 2213 - 2216 (2007/10/02)
Total synthesis of one of Amaryllidaceae alkaloids, hippeastrine, was accomplished starting from methyl 2c-(N-methoxycarbonylamino)-3t-(3,4-methylenedioxyphenyl)cyclohex-4-enyl-r-acetate in stereoselective manner.
