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Towards the total synthesis of mycaperoxide B: probing biosynthetic rationale

Silva, E. M. P., Pye, R. J., Brown, G. and Harwood, L. (2012) Towards the total synthesis of mycaperoxide B: probing biosynthetic rationale. European Journal of Organic Chemistry, 2012 (6). pp. 1209-1216. ISSN 1099-0690

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To link to this article DOI: 10.1002/ejoc.201101477

Abstract/Summary

Studies towards the biomimetic synthesis of mycaperoxide B (1) are described. We have established the synthesis of four diastereoisomers of mycaperoxide B methyl ester (1a) by employing a Michael addition across an α,β-unsaturated ester precursor 2 as the key step. This result strongly suggestsstereocontrol in the addition of the hydroperoxide functionality to the E double bond and discloses the importance of choosing the correct geometry of the α,β-unsaturated double bond when attempting to synthesise mycaperoxide B. Four diastereoisomeric tetrahydrofurans derived from an intramolecular rearrangement of the 1,2-dioxolane enolate 12 were also isolated and characterised.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
Interdisciplinary centres and themes > Chemical Analysis Facility (CAF)
ID Code:27204
Uncontrolled Keywords:Natural products; Biomimetic synthesis; Michael addition; Peroxides; Oxygen heterocycles
Publisher:Wiley

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