Formal synthesis of ent-Cephalotaxine using a one-pot Parham-aldol sequence
Siitonen, J., Yu, L., Danielsson, J., Gregorio, G. D., & Somfai, P. (2018). Formal synthesis of ent-Cephalotaxine using a one-pot Parham-aldol sequence. Journal of Organic Chemistry, 83(18), 11318-11322. https://doi.org/10.1021/acs.joc.8b01540
Published in
Journal of Organic ChemistryDate
2018Copyright
© American Chemical Society, 2018
A short formal synthesis of ent-Cephalotaxine is achieved. The approach features a new Lewis
acid mediated [2,3]-Stevens rearrangement of N-allylated prolineamide to generate a key quaternary
stereogenic center. Additionally, a one-pot Parham–aldol sequence was developed to rapidly assembly two
of the four rings in the cephalotaxine core.
Publisher
American Chemical SocietyISSN Search the Publication Forum
0022-3263Publication in research information system
https://converis.jyu.fi/converis/portal/detail/Publication/28184757
Metadata
Show full item recordCollections
License
Related items
Showing items with similar title or keywords.
-
Synthetic studies on 1-azabicyclo[5.3.0]decane alkaloids
Siitonen, Juha (University of Jyväskylä, 2018)The first chapter introduces the reader to the concept of natural product total synthesis and its importance to chemistry, other sciences, and society. The second chapter reviews the chemistry of natural products ... -
Towards Controlled Synthesis of Water-Soluble Gold Nanoclusters : Synthesis and Analysis
Sokolowska, Karolina; Malola, Sami; Lahtinen, Manu; Saarnio, Ville; Permi, Perttu; Koskinen, Katariina; Jalasvuori, Matti; Häkkinen, Hannu; Lehtovaara, Lauri; Lahtinen, Tanja (American Chemical Society, 2019)Water-soluble gold nanoclusters with well-defined molecular structures and stability possess particular biophysical properties making them excellent candidates for biological applications as well as for fundamental ... -
Water-Soluble Cuprizone Derivative: Synthesis, Characterization, and in Vitro Studies
Fries, Martin; Mertens, Meike; Teske, Nico; Kipp, Markus; Beyer, Cordian; Willms, Thomas; Valkonen, Arto; Rissanen, Kari; Albrecht, Markus; Clarner, Tim (American Chemical Society, 2019)The cuprizone mouse model is one of the most accepted model systems for the investigation of oligodendrocyte degeneration, a process critically involved in the pathogenesis of diseases such as multiple sclerosis or ... -
Asymmetric Synthesis of Dihydropyranones with Three Contiguous Stereocenters by an NHC‐Catalyzed Kinetic Resolution
Axelsson, Anton; Westerlund, Mathias; Zacharias, Savannah C.; Runemark, August; Haukka, Matti; Sundén, Henrik (Wiley, 2021)An oxidative NHC-catalyzed kinetic resolution (KR) of racemic mixtures is presented. The developed reaction furnishes tricyclic dihydropyranones with three contiguous stereocenters in excellent dia- and enantioselectivity, ... -
Synthesis, X-ray Crystal Structure and Antimicrobial Activity of Unexpected Trinuclear Cu(II) Complex from s-Triazine-Based Di-Compartmental Ligand via Self-Assembly
Soliman, M. Saied; Lasri, Jamal; Haukka, Matti; Sholkamy, N. Essam; Al-Rasheed, H. Hessa; El-Faham, Ayman (MDPI, 2019)The synthesis and X-ray crystal structure of the trinuclear [Cu3(HL)(Cl)2(NO3)(H2O)5](NO3)2 complex of the s-triazine-based di-compartmental ligand, 2-methoxy-4,6-bis(2-(pyridin-2-ylmsethylene)hydrazinyl)-1,3,5-triazine ...