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We have established the synthesis of four diastereoisomers of mycaperoxide B methyl ester (<jats:bold>1a<\/jats:bold>) by employing a Michael addition across an \u03b1,\u03b2\u2010unsaturated ester precursor <jats:bold>2<\/jats:bold> as the key step. This result strongly suggestsstereocontrol in the addition of the hydroperoxide functionality to the <jats:italic>E<\/jats:italic> double bond and discloses the importance of choosing the correct geometry of the \u03b1,\u03b2\u2010unsaturated double bond when attempting to synthesise mycaperoxide B. Four diastereoisomeric tetrahydrofurans derived from an intramolecular rearrangement of the 1,2\u2010dioxolane enolate <jats:bold>12<\/jats:bold> were also isolated and characterised.<\/jats:p>","DOI":"10.1002\/ejoc.201101477","type":"journal-article","created":{"date-parts":[[2011,12,27]],"date-time":"2011-12-27T04:12:02Z","timestamp":1324959122000},"page":"1209-1216","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Towards the Total Synthesis of Mycaperoxide B: Probing Biosynthetic Rationale"],"prefix":"10.1002","volume":"2012","author":[{"given":"Eduarda M. 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