American Chemical Society
ol1018163_si_002.pdf (11.03 MB)

Convergent Route to the Spirohexenolide Macrocycle

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journal contribution
posted on 2010-10-15, 00:00 authored by Brian D. Jones, James J. La Clair, Curtis E. Moore, Arnold L. Rheingold, Michael D. Burkart
Using key functional dissections, the synthesis of spirohexenolides is examined through a three-component strategy that features a 1,2-addition to couple tetronate and aldehyde components forming the C2−C3 bond and a Stille coupling to install the third sulfone-containing component. The macrocycle is completed by an intramolecular Julia−Kocienski reaction to form the C10−C11 trans-disubstituted olefin. Application of this strategy is described in progress toward the synthesis of (±)-spirohexenolide B.