Welcome to the new version of CaltechAUTHORS. Login is currently restricted to library staff. If you notice any issues, please email coda@library.caltech.edu
Published November 16, 2012 | Supplemental Material + Accepted Version
Journal Article Open

Enantioselective Synthesis of a Hydroxymethyl-cis-1,3-cyclopentenediol Building Block


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


Files (11.2 MB)
Name Size Download all
2.3 MB Preview Download
8.8 MB Preview Download

Additional details

August 19, 2023
October 20, 2023