Synlett 2013; 24(4): 514-518
DOI: 10.1055/s-0032-1318109
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (–)-Hennoxazole A: Integrating Batch and Flow Chemistry Methods

Amadeo Fernández
a   Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK   Fax: +44(1223)336442   eMail: svl1000@cam.ac.uk
,
Zebulon G. Levine
a   Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK   Fax: +44(1223)336442   eMail: svl1000@cam.ac.uk
,
Marcus Baumann
a   Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK   Fax: +44(1223)336442   eMail: svl1000@cam.ac.uk
,
Sarah Sulzer-Mossé
a   Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK   Fax: +44(1223)336442   eMail: svl1000@cam.ac.uk
,
Christof Sparr
a   Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK   Fax: +44(1223)336442   eMail: svl1000@cam.ac.uk
,
Sabrina Schläger
a   Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK   Fax: +44(1223)336442   eMail: svl1000@cam.ac.uk
,
Albrecht Metzger
a   Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK   Fax: +44(1223)336442   eMail: svl1000@cam.ac.uk
,
Ian R. Baxendale
b   Department of Chemistry, Durham University, South Road, Durham DH1 3LE, UK
,
Steven V. Ley*
a   Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK   Fax: +44(1223)336442   eMail: svl1000@cam.ac.uk
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Publikationsverlauf

Received: 11. Dezember 2012

Accepted: 30. Dezember 2012

Publikationsdatum:
30. Januar 2013 (online)


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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.

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