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.

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