The authors acknowledge financial support by the National Institutes of Health–NIGMS (GM80266 and GM80266-04S1). The authors thank the Periana laboratory for assistance with all hydrogenation reactions, and Prof. Kevin Burgess for helpful discussions in the pursuit of a catalyst-controlled stereoselective hydrogenation.
Convergent Synthesis of Deoxypropionates†
Article first published online: 5 APR 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 21, pages 5152–5156, May 21, 2012
How to Cite
Diez, P. S. and Micalizio, G. C. (2012), Convergent Synthesis of Deoxypropionates . Angew. Chem. Int. Ed., 51: 5152–5156. doi: 10.1002/anie.201200035
- Issue published online: 15 MAY 2012
- Article first published online: 5 APR 2012
- Manuscript Revised: 20 FEB 2012
- Manuscript Received: 2 JAN 2012
- National Institutes of Health. Grant Numbers: GM80266, GM80266-04S1
- convergent coupling;
- total synthesis
Metallacycle-mediated allylic alcohol–alkyne reductive cross-coupling is described as a convergent solution to the synthesis of deoxypropionates. This approach offers superior step-economy in comparison to available strategies based on multistep iterative chain elongation. The technique is demonstrated in a concise synthesis of the C1–C11 subunit of borrelidin, and a total synthesis of (−)-vittatalactone.