Allylation of (R)-2,3-O-Cyclohexylideneglyceraldehyde with 2-Substituted Allylstannanes. Application in the Synthesis of Natural Compounds

The possibility of diastereoselective allylation of (R)-2,3-O-cyclohexylideneglyceraldehyde with methyl 3-[(tributylstannyl)methyl]but-3-enoate and tributyl[2-(2,2-diethoxyethyl)prop-2-en-1-yl]stannane has been demonstrated for the first time. The obtained products have been used to synthesize unsaturated lactones, (6R)- and (6S)-6-[(2R)-1,4-dioxaspiro[4.5]decan-2-yl]-4-methyl-5,6-dihydro-2H-piran-2-ones, that are impor­tant building blocks for the preparation of the C1–C8 fragment of amphidinolides C and F and pheromones of the spring hemlock looper Lambdina athasaria, the pitch pine looper Lambdina pellucidaria, and the coffee leaf miner Leucoptera coffeella.