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Abstract <p>The possibility of diastereoselective allylation of (<i>R</i>)-2,3-<i>O</i>-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, (6<i>R</i>)- and (6<i>S</i>)-6-[(2<i>R</i>)-1,4-dioxaspiro[4.5]decan-2-yl]-4-methyl-5,6-dihydro-2<i>H</i>-piran-2-ones, that are impor­tant building blocks for the preparation of the C<sup>1</sup>–C<sup>8</sup> fragment of amphidinolides C and F and pheromones of the spring hemlock looper <i>Lambdina athasaria</i>, the pitch pine looper <i>Lambdina pellucidaria</i>, and the coffee leaf miner <i>Leucoptera coffeella</i>.</p>

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

  • 期刊论文

  • 发表日期：

    2025年4月1日

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  • V. V. Varanchuk,
  • I. V. Mineyeva

摘要

Abstract

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.