2030-55-9Relevant academic research and scientific papers
Asymmetric Total Syntheses of (?)-α-Lycorane, (?)-Zephyranthine, and Formal Synthesis of (+)-Clivonine
Chen, Yong-Jian,Cai, Sen-Lin,Wang, Chuan-Chuan,Cheng, Jin-Duo,Kramer, S?ren,Sun, Xing-Wen
, p. 1309 - 1313 (2017)
An asymmetric route to (?)-α-lycorane and (?)-zephyranthine, and a formal total synthesis of (+)-clivonine were achieved. A pivotal intermediate, which serves as a potent precursor for the divergent syntheses of these natural products, was accessed by a diastereoselective Pd-catalyzed cinnamylation of an N-tert-butanesulfinyl imine.
Short, enantioselective, gram-scale synthesis of (?)-zephyranthine
Chen, Jingbo,Ma, Guolan,Wei, Qi,Yang, Shaoxiong,Zeng, Xiaoyu,Zhang, Hongbin,Zhao, Yuxiang,Zhu, Yanren
, p. 9452 - 9457 (2021/07/25)
A reasonable synthesis design by strategically integrating functional group manipulation into the ring system construction resulted in a short, enantioselective, gram-scale total synthesis of (?)-zephyranthine. The concise route includes a catalytic Micha
Synthesis and antiviral activity of lycorine derivatives
Yang, Ya-Jun,Liu, Jiang-Ning,Pan, Xian-Dao
, p. 1188 - 1196 (2020/11/19)
There are no effective antiviral drugs to treat hand, foot, and mouth disease. In this study, a series of lycorine derivatives were synthesized and evaluated against enterovirus 71 and coxsackievirus A16 in?vitro. Derivatives 7c-m with the phenoxyacyl gro
Total synthesis of (–)-zephyranthine
Ishii, Koki,Seki-Yoritate, Yuna,Ishibashi, Mizuki,Liaw, Ming Wai,Oishi, Takeshi,Sato, Takaaki,Chida, Noritaka
, p. 111 - 117 (2019/06/24)
– Stereoselective total synthesis of (–)-zephyranthine 1 based on the chiral pool approach starting from D-arabinose is described. The three consecutive chiral centers in (–)-zephyranthine were effectively constructed by the sequential [3,3] sigmatropic r
Preparation of Structurally Diverse Compounds from the Natural Product Lycorine
Tasker, Sarah Z.,Cowfer, Amanda E.,Hergenrother, Paul J.
supporting information, p. 5894 - 5898 (2018/09/25)
The synthesis of a 52-member compound collection from the natural product lycorine is reported, highlighted by divergent cross-coupling and substitution strategies and an unusual ring rearrangement induced by reaction with aryne intermediates.
LYCORINE STRUCTURE-ACTIVITY RELATIONSHIPS
Evidente, Antonio,Cicala, Maria Rosaria,Randazzo, Giacomino,Riccio, Rodolfo,Calabrese, Giuseppe,et al.
, p. 2193 - 2196 (2007/10/02)
Twenty three lycorine derivatives and naturally occurring alkaloids, structurally related to lycorine, were tested for their ability to inhibit ascorbic acid biosynthesis in potato tubers.The following relationships between structure modification and activity were observed: (a) cleavage of the acetalic bonds on the dioxole ring had no effect on activity; (b) derivatives with a methoxy group on C-8 (A ring) were inactive; (c) oxidation of NCH2-7 to an amide group (B ring) caused loss of activity; (d) modification of the C/D ring junction had no effect on activity when the D ring assumed a β configuration whereas a great deciease of activity was observed when that ring assumed an α configuration; (e) selective or complete acetylation of hydroxyl groups of the C ring, epimerization or oxidation of the hydroxyl group on C-2 led to a loss of activity; (f) a compound with a double bond located in the 1,2-position showed activity almost identical to lycorine; (g) stereoselective hydrogenation of the double bond of the C ring induced a considerable increase of the activity; (h) protonation of the nitrogen atom had no effect on activity.Key Word Index- Sternbergia lutea; Amaryllidaceae; alkaloids; lycorine; lycorine derivatives; structure-activity relationships; ascorbate biosynthesis inhibition.
