Macrocyclisation of Macrodiolide with Dimethylaluminium Methaneselenolate

LL Shen, HS Mun, JH Jeong

Index: Shen, Liu-Lan; Mun, Han-Seo; Jeong, Jin-Hyun European Journal of Organic Chemistry, 2010 , # 36 p. 6895 - 6899

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Abstract

Abstract Dimethylaluminium methaneselenolate (Me 2 AlSeMe, 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%.

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