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

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초록

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.

키워드

DIELS-ALDER CYCLOADDITIONSSTILLE COUPLING REACTIONSASYMMETRIC-SYNTHESIS3,5-DIBROMO-2-PYRONEPATHWAYSACCESSARYL
제목
Highly diastereoselective type-I IMDA reaction forming medium-sized macrolactones
저자
Shin, Jeong-TaekHong, Sung-ChoShin, SeunghoonCho, Cheon-Gyu
DOI
10.1021/ol061198g
발행일
2006-07
유형
Article
저널명
Organic Letters
8
15
페이지
3339 ~ 3341