This work was supported by the NSERC. E.A.T. thanks NSERC and FQRNT, and B.M.W. thanks NSERC for postgraduate fellowships.
A Concise Total Synthesis of (R)-Puraquinonic Acid†
Article first published online: 18 FEB 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 12, pages 3442–3445, March 18, 2013
How to Cite
Tiong, E. A., Rivalti, D., Williams, B. M. and Gleason, J. L. (2013), A Concise Total Synthesis of (R)-Puraquinonic Acid . Angew. Chem. Int. Ed., 52: 3442–3445. doi: 10.1002/anie.201208792
- Issue published online: 13 MAR 2013
- Article first published online: 18 FEB 2013
- Manuscript Received: 1 NOV 2012
- puraquinonic acid;
- quaternary stereocenter;
- total synthesis
Distant relative: The configuration of the quaternary stereocenter in puraquinonic acid (see scheme, right) is defined by groups far removed from the point of asymmetry. The use of a bicyclic thioglycolate lactam to set the quaternary stereocenter at an early stage cuts the length of the synthesis of the natural product by nearly two thirds.