2702-54-7Relevant academic research and scientific papers
Total Synthesis of Ovafolinins A and B: Unique Polycyclic Benzoxepin Lignans through a Cascade Cyclization
Davidson, Samuel J.,Barker, David
supporting information, p. 9483 - 9486 (2017/08/01)
Ovafolinins A and B, isolated from Lyonia ovalifolia var. elliptica, are lignans that contain a unique bridged structure containing a penta- and tetracyclic benzoxepin and an aryl tetralin. We report the first total synthesis of these natural products in which an acyl-Claisen rearrangement was initially utilized to construct the lignan backbone with correct relative stereochemistry. Judicious use of a bulky protecting group placed reactive moieties in the correct orientation, thereby resulting in a cascade reaction to form the bridged benzoxepin/aryl tetralin from a linear precursor in a single step. Modification of this route allowed the enantioselective synthesis of (+)-ovafolinins A and B, which confirmed the absolute stereochemistry, and comparison of optical rotation suggests that these compounds are found as scalemic mixtures in nature.
Development of synthetic methodology suitable for the radiosynthesis of combretastatin A-1 (CA1) and its corresponding prodrug CA1P
Shirali, Anupama,Sriram, Madhavi,Hall, John J.,Nguyen, Benson L.,Guddneppanavar, Rajsekhar,Hadimani, Mallinath B.,Ackley, J. Freeland,Siles, Rogelio,Jelinek, Christopher J.,Arthasery, Phyllis,Brown, Rodney C.,Murrell, Victor Leon,McMordie, Austin,Sharma, Suman,Chaplin, David J.,Pinney, Kevin G.
experimental part, p. 414 - 421 (2009/12/05)
Synthetic methodology has been established suitable for the preparation of combretastatin A-1 (CA1) and its corresponding phosphate prodrug salt (CA1P) in high specific activity radiolabeled form. Judicious selection of appropriate phenolic protecting groups to distinguish positions on the A-ring from the B-ring of the stilbenoid was paramount for the success of this project. Methylation of the C-4' phenolic moiety by removal of the tert- butyldimethylsilyl protecting group in the presence of methyl iodide was accomplished in excellent yield without significant Z to E isomerization. This step (carried out with 12C-methyl iodide as proof of concept in this study) represents the process in which a 14C radioisotope could be incorporated in an actual radiosynthesis. CA1 is a natural product isolated from the African bush willow tree (Combretum caffrum) that has important medicinal value due, in part, to its ability to inhibit tubulin assembly. As a prodrug, CA1P (OXi4503) is in human clinical trials as a vascular disrupting agent.
Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 1. Mescalin derivatives
Trachsel, Daniel
, p. 3019 - 3026 (2007/10/03)
The synthesis and the spectroscopic data of 14 novel 4-substituted mescaline derivatives are reported. Starting from syringaldehyde (=4-hydroxy-3,5-dimethoxybenzaldehyde), several ethers were obtained from reaction with a series of corresponding saturated and unsaturated alkyl- and fluoroalkyl halides. Henry-reaction with MeNO2 or EtNO2 followed to afford the nitro-olefines, which were then reduced with AlH3 to the desired 2-phenytethyl- and 1-methyl-2-phenylethylamine derivatives.
