We gratefully acknowledge financial support from the NIGMS CMLD initiative (P50-GM067041) and the National Science Foundation (CHE 0750273). We thank Prof. Aaron B. Beeler for assistance with conformational analysis and Prof. Corey R. J. Stephenson, Dr. Paul Ralifo, Dr. Norman Lee, and Dr. Jeff Bacon (Boston University) for helpful discussions and assistance with NMR spectroscopy, HRMS, and X-ray measurements.
Sequential Transformations to Access Polycyclic Chemotypes: Asymmetric Crotylation and Metal Carbenoid Reactions†
Article first published online: 10 MAY 2011
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 50, Issue 26, pages 5938–5942, June 20, 2011
How to Cite
Wu, J., Becerril, J., Lian, Y., Davies, H. M. L., Porco, J. A. and Panek, J. S. (2011), Sequential Transformations to Access Polycyclic Chemotypes: Asymmetric Crotylation and Metal Carbenoid Reactions. Angew. Chem. Int. Ed., 50: 5938–5942. doi: 10.1002/anie.201101366
- Issue published online: 15 JUN 2011
- Article first published online: 10 MAY 2011
- Manuscript Received: 23 FEB 2011
- NIGMS CMLD initiative. Grant Number: P50-GM067041
- National Science Foundation. Grant Number: CHE 0750273
- diversity-oriented synthesis;
- sequential transformations
All in order: Bicyclic and tricyclic chemotypes were accessed through the title transformations. By subsequent pairing of installed functional groups using Heck cyclization or [2+2] photocycloaddition, the synthesis of tetracycles, pentacycles, and condensed polycycles has been achieved with high stereochemical and skeletal variation.