Synthesis of (-)-morphine: Application of sequential claisen/claisen rearrangement of an allylic vicinal diol

Masato Ichiki, Hiroki Tanimoto, Shohei Miwa, Ryosuke Saito, Takaaki Sato, Noritaka Chida

研究成果: Article査読

35 被引用数 (Scopus)

抄録

A detailed exploration of the synthesis of (-)-morphine based on sequential [3,3]-sigmatropic rearrangements is described. The sequential Claisen/Claisen rearrangements of an allylic vicinal diol resulted in the stereoselective formation of the two contiguous carbon centers, including a sterically encumbered quaternary carbon, in a single operation. The two ethyl esters generated in this reaction were successfully differentiated during a subsequent Friedel-Crafts-type cyclization. The (-)-morphine double bond was introduced at a late stage in our first-generation synthesis, but was formed at an earlier stage in the second-generation synthesis, resulting in a more efficient route to the end product.

本文言語English
ページ(範囲)264-269
ページ数6
ジャーナルChemistry - A European Journal
19
1
DOI
出版ステータスPublished - 2013 1 2

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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