Scholarlink

Abstract <p>The synthesis of a bicyclic allyl acetate, a promising precursor of (–)-galiellalactone, is performed. The synthetic approach is based on separation of the diastereomeric carboxamides prepared by the amidation of racemic <i>gem</i>-dichloro-substituted Grieco lactone with (+)-α-methylbenzylamine. The subsequent steps of transformation of an individual diastereomer involve complete reductive dechlorination, construction of an allyl alcohol fragment in the ring part by stereo- and regiospecific bromohydroxylation with NBS in aqueous THF, and dehydrobromination.</p>

错误：搜索内容不能为空，请输入英文关键词
错误：关键词超出字数限制，请精简
高级检索

Synthesis of (3aS,4S,6aR)-2-Oxo-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-4-yl Acetate as a Key Synthon for (–)-Galiellalactone

  • 期刊论文

  • 发表日期：

    2025年2月1日

查看全文
  • A. M. Gimazetdinov,
  • V. V. Zagitov,
  • Z. R. Makaev,
  • M. S. Miftakhov

摘要

Abstract

The synthesis of a bicyclic allyl acetate, a promising precursor of (–)-galiellalactone, is performed. The synthetic approach is based on separation of the diastereomeric carboxamides prepared by the amidation of racemic gem-dichloro-substituted Grieco lactone with (+)-α-methylbenzylamine. The subsequent steps of transformation of an individual diastereomer involve complete reductive dechlorination, construction of an allyl alcohol fragment in the ring part by stereo- and regiospecific bromohydroxylation with NBS in aqueous THF, and dehydrobromination.