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Synfacts 2010(7): 0758-0758  
DOI: 10.1055/s-0029-1220135
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Dihydropyranone Synthesis Using a Sonogashira Coupling

Contributor(s): Victor Snieckus, Johnathan Board
H. Fuwa*, S. Matsukida, M. Sasaki
Tohoku University, Sendai, Japan
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Publication History

Publication Date:
22 June 2010 (online)

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Significance

Reported is the synthesis of di­hydropyranones from para-toluene thiol esters via a Sonogashira deprotection-cyclization sequence. Aside from the indicated stoichiometry for the cyclizations, it was also demonstrated that it may be performed with substoichiometric (10 mol%) quantities of silver triflate without a reduction in the yield. However, under these conditions the reaction time increased to 9.4 hours.