Abstract <p>Unsaturated lactones, (6<i>R</i>)- and (6<i>S</i>)-6-[(2<i>R</i>)-1,4-dioxaspiro[4.5]dec-2-yl]-4-methyl-5,6-dihydro-2<i>H</i>-pyran-2-ones, have been synthesized by diastereoselective allylation of (<i>R</i>)-2,3-<i>O</i>-cyclohexylidene­glycer­aldehyde with methyl 3-(bromomethyl)but-3-enoate and its allylstannyl derivative. These lactones have been subjected to highly diastereoselective reduction and utilized in a new retrosynthetic scheme for obtaining C<sup>5</sup>–C<sup>14</sup>, C<sup>15</sup>–C<sup>19</sup>, and C<sup>20</sup>–C<sup>26</sup> building blocks of amphidinolide G and H families.</p>

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Synthesis of Principal Building Blocks of Amphidinolides of the G and H Families

  • I. V. Mineyeva

摘要

Abstract

Unsaturated lactones, (6R)- and (6S)-6-[(2R)-1,4-dioxaspiro[4.5]dec-2-yl]-4-methyl-5,6-dihydro-2H-pyran-2-ones, have been synthesized by diastereoselective allylation of (R)-2,3-O-cyclohexylidene­glycer­aldehyde with methyl 3-(bromomethyl)but-3-enoate and its allylstannyl derivative. These lactones have been subjected to highly diastereoselective reduction and utilized in a new retrosynthetic scheme for obtaining C5–C14, C15–C19, and C20–C26 building blocks of amphidinolide G and H families.