A skipped diene（1,4-diene）is an important structural motif found in a variety of biologically active natural products. We report the stereodivergent method, consisting of hydroboration of allenes and the Migita-Kosugi-Stille coupling, which allows for access to all four possible stereo-isomers of the skipped dienes. The hydroboration of allenes is especially useful because both E-allylic and Z-allylic alcohols are obtained by simply changing the organoborane reagent. While use of 9-BBN provides E-allylic alcohols as thermodynamic products, the reaction with HB（Sia）2 gives Z-allylic alcohols as kinetic products. The developed method was successfully applied to the unified total synthesis of madangamine alkaloids.
|Translated title of the contribution||Development of Stereodivergent Synthesis of Skipped Dienes and Application to Unified Total Synthesis of Madangamine Alkaloids|
|Number of pages||14|
|Journal||Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry|
|Publication status||Published - 2022|
ASJC Scopus subject areas
- Organic Chemistry