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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

Amadeo Fernandez

Zebulon G. Levine

Marcus Baumann

Sarah Sulzer-Mosse

Christof Sparr

Sabrina Schlaeger

Albrecht Metzger

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