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2005
Furan derivatives
R 0060
Regioselective Synthesis of 1,7-Dioxaspiro[4.4]nonanes from a TrimethyleneDianion Synthon. — Compound (I) behaves as a versatile trimethylene32- 115 methane
methane dianion synthon under arene-catalyzed lithiation conditions. A variety of
methylidenic diols is obtained in the presence of ketones or aldehydes, followed by
addition of an epoxide and final hydrolysis. These diols undergo double intramolecular
iodoetherification to give the desired spiro compounds, which can be oxidized to the
corresponding lactones. In the appropriate cases, excellent stereoselectivities are
achieved besides high yields and regioselectivities. — (ALONSO, F.; DACUNHA, B.;
MELENDEZ, J.; YUS*, M.; Tetrahedron 61 (2005) 13, 3437-3450; Dep. Quim. Org.,
Fac. Cienc., Univ. Alicante, E-03080 Alicante, Spain; Eng.) — Klein
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