Published Online: 15 SEP 2010
Copyright © 2010 John Wiley & Sons, Inc. All rights reserved.
Comprehensive Organic Name Reactions and Reagents
How to Cite
2010. Ghosez Cyclization. Comprehensive Organic Name Reactions and Reagents. 268:1217–1220.
- Published Online: 15 SEP 2010
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The synthesis of α,β-unsaturated δ-lactone and the corresponding dihydropyran reduced from such lactone derivative, involving the reaction of epoxide with the lithio derivative of methyl 3-(phenylsulfonyl)orthopropionate and subsequent acid hydrolysis and base-induced elimination of phenylsulfinic acid, is known as the Ghosez cyclization. The methyl 3-(phenylsulfonyl)orthopropionate functions as a 1,3-dipole equivalent in this reaction. A similar reaction involving 2,3-dibromo-1-phenylsulfonyl-1-propene and a carbanion from acetoacetone has also been represented. This reaction has certain applications in organic synthesis, such as the preparation of hydrindan, glycoside, and natural product swinholide A.
- methyl 3-(phenylsulfonyl)orthopropionate;
- acidic hydrolysis;
- phenylsulfinic acid