Macrocyclisation of macrodiolide with dimethylaluminium methaneselenolate

Liu Lan Shen, Han Seo Mun, Jin Hyun Jeong

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Dimethylaluminium methaneselenolate (Me2AlSeMe, 1) acts as an acyl transfer agent for esterification. In cases of direct macrolactonisation (n = 10-12), this selenium-aluminium complex preferentially creates symmetric macrodiolides rather than macrolides. The factors determining macrodilactonisation were investigated and applied toward the total synthesis of norpyrenophorin, which result in a macrodilactonisation yield of 64 %. Dimethylaluminium methaneselenolate (Me2AlSeMe, 1) acts as an acyl transferagent for esterification. In cases of direct macrolactonisation (n = 10-12), this selenium-aluminium complex preferentiallycreates symmetric macrodiolides rather than macrolides. The factors determining macrodilactonisation were investigated and applied toward the total synthesis of nor-pyrenophorine.

Original languageEnglish
Pages (from-to)6895-6899
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number36
DOIs
Publication statusPublished - 2010 Dec

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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