Structure of Julocrotine^1,2

Three new Glutarimide Alkaloids fromCroton Cuneatus

“…In fact, selective irradiation at 6.00 (H-14) enchanted the signals of the aromatic carbons C-16, C-20, and irradiation at 3.90 (H-13a) gave response for C-14 and C-15. Based on a reported procedure [8,9], the acid hydrolysis of 1 afforded three compounds identified by their NMR spectra and optical rotations as: (þ) glutamic acid, (þ)-2-methylbutanoic acid, and (þ)-2-amino-1-phenylethanol. Since the spectral data and the optical rotation of one of our hydrolysis products matched the data reported for (S)-2-amino-1-phenylethanol [10][11][12], the stereocenter C-14 of 1 was assigned as (S).…”

Glutarimide Alkaloids Through Multicomponent Reaction Chemistry

“…Glutarimide -containing polyketides have shown cell migration inhibitory activity, [6] and glutarimide macroketones are effective against cancer metastasis. [8] The structure of julocrotine was elucidated in 1961 with a series of degradation reactions [9] and a report in 1974 showed the synthesis of a lower homologue using harsh conditions. The scaffold is present in the structure of julocrotine, which has shown antiproliferative effects in in vitro tests against the promastigote and amastigote forms of Leishmania amazonensis.…”

“…The scaffold is present in the structure of julocrotine, which has shown antiproliferative effects in in vitro tests against the promastigote and amastigote forms of Leishmania amazonensis. [8] The structure of julocrotine was elucidated in 1961 with a series of degradation reactions [9] and a report in 1974 showed the synthesis of a lower homologue using harsh conditions. [10] In 2011, a six step synthesis starting from L-glutamic acid was described.…”

Synthesis of Triazolyl‐Substituted Quinolizidine Imides

“…4 We have reported some synthetic applications of this method, 5 and have studied some of their biological activities. 6 It has been reported that cyclic imides such as migrastatin, 7 thalidomide, 8 and julocrotine 9 have very useful biological activities. Some bicyclic imides including rolziracetam 10 and benzo-fused compounds 4 and 5 have the potential for treating Alzheimer's disease (Scheme II).…”