10.1055/s-0029-1216990
The research focuses on the enantiospecific synthesis of a novel rearranged eunicellane diterpenoid using SmI2-mediated cyclization. The study investigates the synthesis and cyclization of α-geranylated carvones to assemble marine-derived diterpenoids. Key reactants include side-chain hydrogenated carvone, geraniol-derived aldehydes, and samarium diiodide (SmI2). The experiments involve 3-hydroxyalkylation, retro-aldol fragmentation, and NOESY-based structure analysis to reveal the presence of an ansa bridge across a twist-boat six-membered ring in the synthesized diterpenoid. Analytical techniques used in the study include NMR, IR, MS, UV/Vis spectroscopy, and X-ray crystallography to confirm the structures and properties of the synthesized compounds. The research provides insights into the assembly of eunicellane-type diterpenoids and introduces a novel skeletal structure, isoeunicellane, with potential for further structural variations.
10.1080/14786419.2015.1075525
The research focuses on the utilization of hydrotalcite catalysis for the synthesis of novel chiral building blocks, specifically lactones 7 and 8, derived from carvone. The methodology involves a regioselective Baeyer–Villiger reaction using hydrogen peroxide as the oxidant and hydrotalcites as catalysts, which is considered green due to the lack of by-products other than water. The study compares different reaction conditions, including the use of AlCl3 and meta-chloroperbenzoic acid (m-CPBA) as oxidants, and evaluates the efficiency of the catalysts in terms of yield and selectivity. Reactants such as carvone, benzonitrile, and various catalysts were used, and the progress of reactions was monitored by thin-layer chromatography (TLC). Analyses of the synthesized compounds were conducted using techniques like infrared spectroscopy (IR), nuclear magnetic resonance (NMR), and high-resolution mass spectrometry (HRMS) to determine their structures and confirm their formation.
