立 体 発 散 的 ス キ ッ プ ジ エ ン 合 成 法の 開 発 と マ ダ ン ガ ミ ン 類 の 網 羅 的全 合 成

Translated title of the contribution: Development of Stereodivergent Synthesis of Skipped Dienes and Application to Unified Total Synthesis of Madangamine Alkaloids

Research output: Contribution to journalArticlepeer-review

Abstract

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 contributionDevelopment of Stereodivergent Synthesis of Skipped Dienes and Application to Unified Total Synthesis of Madangamine Alkaloids
Original languageJapanese
Pages (from-to)343-356
Number of pages14
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume80
Issue number4
DOIs
Publication statusPublished - 2022

ASJC Scopus subject areas

  • Organic Chemistry

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