Methyl 3-bromomethyl-3-butenoate as an isopentane building block for the stereoselective preparation of (S)-4-methyl-3,6-dihydro-2H-pyran-2-carbaldehyde and (+)-faranal

(S)-4-Methyl-3,6-dihydro-2H-pyran-2-carbaldehyde (3), the common intermediate in the syntheses of the C17-C27 subunit of laulimalide (4) and (+)-faranal (5), the trail pheromone of the pharaoh ant, Monomorium pharaonis, were obtained via transformation of methyl 3-bromomethyl-3-butenoate (1) into allylstannane 2 and subsequent allylation of (benzyloxy)acetaldehyde (6) in accordance with the Keck procedure as the key steps.     

Allylation of Ketones with Methyl 3-(Bromomethyl)but-3-enoate. Synthesis of Bioactive Unsaturated Lactones Based on Benzo[f]coumarin and Its Derivatives

Russian Journal of Organic Chemistry - Efficient procedures have been developed for the allylation of structurally diverse ketones with methyl 3-(bromomethyl)but-3-enoates, and the possibility of...     

Functionalized 2-Substituted Allyl Bromides in the Barbier Allylation of (R)-2,3-O-Isopropylideneglyceraldehyde. Synthesis of the C8–C17, C8–C18, and C5–C17 Building Blocks of Laulimalides and Their Synthetic Analogs

Russian Journal of Organic Chemistry - Several new 2-substituted allyl bromides were synthesized through cyclopropanol intermediates and were then involved in the Barbier allylation of...     

α,β-Unsaturated β-Methyl-δ-lactones in Nitrile Oxide Cycloaddition Reactions. Synthesis of Saturated Lactones and Lactams

Russian Journal of Organic Chemistry - New isoxazoline derivatives have been synthesized in high yields by cycloaddition of acetonitrile oxide to α,β-unsaturated...     

New 1,4-Dihydropyridines. Optimization of the Synthesis and In Silico Analysis of Biological Activity

Russian Journal of Organic Chemistry - An efficient procedure has been developed for the synthesis of 1,4-dihydropyridines containing aliphatic and 2-(1-hydroxycyclopropyl)methyl substituents via...