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other · Comprehensive Organic Name Reactions and Reagents · 2010

Ghosez Cyclization

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Abstract

Abstract 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.

Cite this paper

APA 7

(2010). Ghosez Cyclization. Comprehensive Organic Name Reactions and Reagents, 1217–1220. https://doi.org/10.1002/9780470638859.conrr268

MLA 9

“Ghosez Cyclization.” Comprehensive Organic Name Reactions and Reagents, 2010, pp. 1217–20, https://doi.org/10.1002/9780470638859.conrr268.

Chicago

2010. “Ghosez Cyclization.” Comprehensive Organic Name Reactions and Reagents: 1217–20. https://doi.org/10.1002/9780470638859.conrr268.

Harvard

(2010) ‘Ghosez Cyclization’, Comprehensive Organic Name Reactions and Reagents, pp. 1217–1220. Available at: https://doi.org/10.1002/9780470638859.conrr268.

BibTeX
@misc{anon2010ghosez,
  title = {{Ghosez Cyclization}},
  journal = {Comprehensive Organic Name Reactions and Reagents},
  pages = {1217--1220},
  year = {2010},
  doi = {10.1002/9780470638859.conrr268}
}

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