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2005
Pyran derivatives
R 0340
Highly Substituted Tetrahydropyrones from Hetero-Diels—Alder Reactions of
with Stereochemical Induction from Chiral Dienes. — A new and
34- 181 2-Alkenals
stereoselective route to all-cis 2,3,6-trisubstituted tetrahydropyrones, versatile building
blocks, is reported. These pyrones can easily be converted into tertiary pyranols such
as (X) and smoothly undergo base-promoted epimerization at C-3. In contrast, the
aromatic diene (XII) reacts with α,β-unsaturated aldehydes to afford classical
Diels—Alder products. The expected hetero-Diels—Alder cycloadducts are not
formed. — (RUIJTER, E.; SCHUELTINGKEMPER, H.; WESSJOHANN*, L. A.; J.
Org. Chem. 70 (2005) 7, 2820-2823; Inst. Pflanzenbiochem., Leibniz Inst.,
D-06120 Halle/S., Germany; Eng.) — Jannicke
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