Published November 16, 2012
| Supplemental Material + Accepted Version
Journal Article
Open
Enantioselective Synthesis of a Hydroxymethyl-cis-1,3-cyclopentenediol Building Block
Abstract
A brief, enantioselective synthesis of a hydroxymethyl-cis-1,3-cyclopentenediol building block is presented. This scaffold allows access to the cis-1,3-cyclopentanediol fragments found in a variety of biologically active natural and non-natural products. This rapid and efficient synthesis is highlighted by the utilization of the palladium-catalyzed enantioselective allylic alkylation of dioxanone substrates to prepare tertiary alcohols.
Additional Information
© 2012 American Chemical Society. Received October 2, 2012. Publication Date (Web): October 26, 2012. The authors wish to thank NIH-NIGMS (R01GM080269-01), NIH Grant F32GM082000 (postdoctoral fellowship to A.C.J.), the California Tobacco-Related Disease Research Program of the University of California, Grant Number 14DT-0004 (predoctoral fellowship to J.L.R.), Amgen, Abbott, Boehringer Ingelheim, and Caltech for financial support. Dr. Nathaniel Sherden, Dr. Masaki Seto, Dr. Pamela Tadross, Dr. Scott Virgil, Mr. Jeffery Holder, Mr. Corey Reeves, and Ms. Amanda Silberstein (Caltech) are thanked for helpful discussions and experimental support.Attached Files
Accepted Version - nihms418193.pdf
Supplemental Material - ol3027297_si_001.pdf
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nihms418193.pdf
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Additional details
- PMCID
- PMC3506031
- Eprint ID
- 36201
- DOI
- 10.1021/ol3027297
- Resolver ID
- CaltechAUTHORS:20130107-104400691
- NIH
- R01GM080269-01
- NIH Postdoctoral Fellowship
- F32GM082000
- California Tobacco-Related Disease Research
- 14DT-0004
- Amgen
- Abbott
- Boehringer Ingelheim
- Caltech
- Created
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2013-01-07Created from EPrint's datestamp field
- Updated
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2021-11-09Created from EPrint's last_modified field