Publication:
Synthesis of gem-difluoromethylenated bicyclo[ m.n. 0]alkan-1-ols and their ring-expansion to gem-difluoromethylenated macrocyclic lactones

Issued Date

2012-04-06

Resource Type

Article

ISSN

15237052
15237060

DOI

10.1021/ol3004194

Other identifier(s)

2-s2.0-84859567131

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Organic Letters. Vol.14, No.7 (2012), 1820-1823

Suggested Citation

Teerachai Punirun, Krisana Peewasan, Chutima Kuhakarn, Darunee Soorukram, Patoomratana Tuchinda, Vichai Reutrakul, Palangpon Kongsaeree, Samran Prabpai, Manat Pohmakotr Synthesis of gem-difluoromethylenated bicyclo[ m.n. 0]alkan-1-ols and their ring-expansion to gem-difluoromethylenated macrocyclic lactones. Organic Letters. Vol.14, No.7 (2012), 1820-1823. doi:10.1021/ol3004194 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/13760

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Title

Synthesis of gem-difluoromethylenated bicyclo[ m.n. 0]alkan-1-ols and their ring-expansion to gem-difluoromethylenated macrocyclic lactones

Author(s)

Teerachai Punirun
 Krisana Peewasan
 Chutima Kuhakarn
 Darunee Soorukram
 Patoomratana Tuchinda
 Vichai Reutrakul
 Palangpon Kongsaeree
 Samran Prabpai
 Manat Pohmakotr

Other Contributor(s)

Mahidol University

Abstract

Fluoride-catalyzed stereoselective nucleophilic addition of PhSCF 2 SiMe 3 (1) to α-carboethoxycycloalkanones 2 followed by intramolecular radical cyclization of the resulting cis-3 adduct afforded the corresponding gem-difluoromethylenated bicyclic compounds 4, which underwent ring-expansion followed by the Baeyer-Villiger-type oxidation of the resulting macrocyclic ketone intermediates to give gem-difluoromethylenated macrocyclic lactones 5. © 2012 American Chemical Society.

Keyword(s)

Biochemistry, Genetics and Molecular Biology
 Chemistry

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URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/13760

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