119906-63-7Relevant academic research and scientific papers
Total synthesis and complete assignment of the stereostructure of a cytotoxic bromotriterpene polyether (+)-aurilol
Morimoto, Yoshiki,Nishikawa, Yoshihiro,Takaishi, Mamoru
, p. 5806 - 5807 (2005)
The plane structure and partial stereochemistry of a cytotoxic bromotriterpene polyether (+)-aurilol (1), isolated from the sea hare Dolabella auricularia, were mainly elucidated by NMR methods; however, determination of the entire stereochemistry has not been reached. Although there have also been many other types of triterpene polyethers, it is often difficult to determine their stereostructures even by the current highly advanced spectroscopic methods, especially in acyclic systems including quaternary carbon centers such as C10-C11, C14-C15, and C18-C19 in 1. In this paper, we report that the total assignment of the incomplete stereostructure of (+)-aurilol (1) to the structural formula 2 has been accomplished through its first asymmetric total synthesis featuring the highly regio- and stereocontrolled biogenetic-like A-D ether ring formations. Copyright
Divergent synthesis of four isomers of 6,7-dihydroxy-3,7-dimethyloct-2-enoic acid, esters and evaluation for the antifungal activity
Wang, Weiwei,Zhang, Xiaoteng,Zhao, Yu,Liu, Xinlei,Zhang, Zhenhua,Wang, Mingan
supporting information, (2018/03/12)
The four isomers of 6,7-dihydroxy-3,7-dimethyloct-2-enoic acid 2 were synthesized via the selective direct Sharpless asymmetry dihydroxylation of geraniol as the key step in 35.0%-48.0% overall yields with 91.9%-97.7% ee values for esters 4 and 31.3%-36.4% overall yields with 90.3-97.5% ee values for acids 2 using cis- and trans-geraniol as raw materials. Their structures were characterized by 1H, 13C NMR and HR-ESI-MS data. The in vivo bioassay results showed that the chiral acid (Z, S)-2 was a good lead compound with 80%-100% inhibitory rates against P. cubensis, E. graminis, P. sorghi and C. gloeosporioides at the concentration of 400μg/mL.
Asymmetric synthesis and structure-activity studies of the fungal metabolites colletorin A, colletochlorin A and their halogenates analogues
Marsico, Giulia,Pignataro, Barbara A.,Masi, Marco,Evidente, Antonio,Casella, Francesca,Zonno, Maria Chiara,Tak, Jun-Hyung,Bloomquist, Jeffrey R.,Superchi, Stefano,Scafato, Patrizia
, p. 3912 - 3923 (2018/06/08)
The first asymmetric total synthesis of both enantiomers of the natural products colletorin A and colletochlorin A is presented. The proposed methodology is based on the coupling reaction between highly substituted aromatic Gilman cuprates and optically active allyl bromides, in turn obtained by Sharpless asymmetric dihydroxylation. The latter ensured a high degree of regio- and stereocontrol in the enantioselective step of the synthesis. The same synthetic strategy has been also applied for the preparation of differently halogenated synthetic analogues of colletochlorin A in high enantiomeric purity. The enantioselective synthesis of colletorin A and colletochlorin A allows to reliably assign their absolute configuration. Preliminary assessment of their herbicidal and insecticidal properties evidence the possibility to modulate the bioactivity of these compounds, highlighting its dependence on both the absolute stereochemistry and the halogen nature.
A synthetic study on antiviral and antioxidative chromene derivative
Mori, Jun,Iwashima, Makoto,Takeuchi, Makoto,Saito, Haruo
, p. 391 - 396 (2007/10/03)
An efficient synthesis of the antiviral and antioxidative chromene (1) was achieved. A small amount of chromene 1 could be derived from plastoquinones 2 and 3, the major constituents of the brown alga, Sargassum micracanthum. By the following synthetic sc
