Macrocyclisation of macrodiolide with dimethylaluminium methaneselenolate

Liu Lan Shen, Han Seo Mun, Jin-Hyun Jeong

Research output: Contribution to journalArticle

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 1

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Macrolides
Esterification
Selenium
selenium
Aluminum
aluminum
synthesis

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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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.",
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Macrocyclisation of macrodiolide with dimethylaluminium methaneselenolate. / Shen, Liu Lan; Mun, Han Seo; Jeong, Jin-Hyun.

In: European Journal of Organic Chemistry, No. 36, 01.12.2010, p. 6895-6899.

Research output: Contribution to journalArticle

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