Synthesis of (-)-hennoxazole A: integrating batch and flow chemistry methods

 

 

Synthesis of (-)-hennoxazole A: integrating batch and flow chemistry methods

A. Fernández, Z.G. Levine, M. Baumann, S. Sulzer-Mossé, C. Sparr, S. Schläger, A. Metzger, I.R. Baxendale, S.V. Ley,Synlett, 2013, 24, 514-518.

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.

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https://www.thieme-connect.de/DOI/DOI?10.1055/s-0032-1318109