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Highly diastereoselective type-I IMDA reaction forming medium-sized macrolactones

Jeong-Taek Shin1, Sung-Cho Hong, Seunghoon Shin

  • 1Department of Chemistry, Hanyang University, 133-791 Seoul, South Korea.

Organic Letters
|July 14, 2006
PubMed
Summary

Intramolecular Diels-Alder reactions using alkyne-tethered 2-pyrones yield medium-sized macrolactones with high selectivity. Conformational bias from a single methyl group in the tether drives this stereochemical control in strained macrocyclic systems.

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