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200517.fm Page 146 Friday, March 18, 2005 2:52 PM
2005
Pyran derivatives
R 0340
Alkynyltrifluoroborates as Versatile Tools in Organic Synthesis: A New Route to
— The key elements in the approach involve the use of lithium alkynyl17- 133 Spiroketals.
trifluoroborates to convert lactones (I) and (XII) into benzyl-protected hydroxyl
α-alkynones. This step is followed by a one-pot cascade consisting of palladium-catalyzed hydrogenation of the triple bond, hydroxyl group deprotection, and spirocyclization under mild nonacidic conditions. Both sequences proceed with high yields. —
(DOUBSKY, J.; STREINZ, L.; SAMAN, D.; ZEDNIK, J.; KOUTEK*, B.; Org. Lett.
6 (2004) 26, 4909-4911; Inst. Org. Chem. Biochem., Acad. Sci. Czech Rep.,
CZ-166 10 Prague 6, Czech Republic; Eng.) — Steudel
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