American Chemical Society
ol061198g_si_001.pdf (3.77 MB)

Highly Diastereoselective Type-I IMDA Reaction Forming Medium-Sized Macrolactones

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journal contribution
posted on 2006-07-20, 00:00 authored by Jeong-Taek Shin, Sung-Cho Hong, Seunghoon Shin, Cheon-Gyu Cho
Intramolecular Diels−Alder (IMDA) reactions of 2-pyrones containing an alkyne tether occur with remarkably high diastereofacial selectivity to provide medium-sized macrolactones. Because of the strain in the alkyne-tethered macrocyclic system, a single methyl group in the tether provides sufficient conformational bias to generate medium-sized macrocycles with unusually high selectivity.