Accessibility navigation

Towards the total synthesis of mycaperoxide B: probing biosynthetic rationale

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

Full text not archived in this repository.

It is advisable to refer to the publisher's version if you intend to cite from this work. See Guidance on citing.

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


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
Divisions: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

University Staff: Request a correction | Centaur Editors: Update this record

Page navigation