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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 5
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Original Articles

New Synthesis of 2,2‐Bis(hydroxymethyl) methylenecyclopropane, a Key Intermediate for Antiviral Cyclopropavir

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Pages 697-702 | Received 05 Sep 2007, Published online: 15 Feb 2008
 

Abstract

Synthesis of 2,2‐bis(hydroxymethyl)methylenecyclopropane (2) is described. Cyclopropane dicarboxylate 3 was reduced to diol 4, which was acetylated to give diacetate 5. Acetoxy‐bromo elimination afforded methylenecyclopropane 6. Debenzylation gave the title compound 2.

Acknowledgments

We thank L. M. Hryhorczuk from the Central Instrumentation Facility, Department of Chemistry, Wayne State University, for mass spectra. The work described herein was supported by SBIR Grant 5 R44 AI0554135 to Microbiotix, Inc., Worcester, Massachusetts, and Research Grant 1 RO1 CA32779 from the National Institutes of Health, Bethesda, Maryland, USA.

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