Amadeo Fernandez
Synthesis of (-)-Hennoxazole A: Integrating Batch and Flow Chemistry Methods
Fernandez, Amadeo; Levine, Zebulon G.; Baumann, Marcus; Sulzer-Mosse, Sarah; Sparr, Christof; Schlaeger, Sabrina; Metzger, Albrecht; Baxendale, Ian R.; Ley, Steven V.
Authors
Zebulon G. Levine
Marcus Baumann
Sarah Sulzer-Mosse
Christof Sparr
Sabrina Schlaeger
Albrecht Metzger
Professor Ian Baxendale i.r.baxendale@durham.ac.uk
Professor
Steven V. Ley
Abstract
A new total synthesis of (–)-hennoxazole A is reported. The synthetic approach is based on the preparation of three similarly sized fragments resulting in a fast and convergent assembly of the natural product. The three key reactions of the synthesis include a highly stereoselective 1,5-anti aldol coupling, a gold-catalyzed alkoxycyclization reaction, and a stereocontrolled diene cross-metathesis. The synthesis involves integrated batch and flow chemistry methods leading to the natural product in 16 steps longest linear sequence and 2.8% overall yield.
Citation
Fernandez, A., Levine, Z. G., Baumann, M., Sulzer-Mosse, S., Sparr, C., Schlaeger, S., …Ley, S. V. (2013). Synthesis of (-)-Hennoxazole A: Integrating Batch and Flow Chemistry Methods. Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, 24(4), 514-518. https://doi.org/10.1055/s-0032-1318109
Journal Article Type | Article |
---|---|
Publication Date | 2013-03 |
Deposit Date | Jul 14, 2014 |
Journal | Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry |
Print ISSN | 0936-5214 |
Electronic ISSN | 1437-2096 |
Publisher | Thieme Gruppe |
Peer Reviewed | Peer Reviewed |
Volume | 24 |
Issue | 4 |
Pages | 514-518 |
DOI | https://doi.org/10.1055/s-0032-1318109 |
Public URL | https://durham-repository.worktribe.com/output/1457051 |
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