Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 5, Pages 1740-1743Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo902167r
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Funding
- Polish Ministry of Education and Science [PBZ-K BN-12/T9/2004]
- Foundation for Polish Science
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This paper presents a simple and efficient route to chiral cis-6-substituted 2-(2-hydroxyethyl)-5,6-dihydro-2H-pyrans, a versatile chiral building block. The strategy is based on three key transformations: enantioselective hetero-Diels-Alder (HDA) reaction of aldehyde with Danishekky's diene, selective reduction of carbonyl function, and Claisen or related rearrangement. The synthetic utility of the methodology is illustrated by toal synthesis of antibiotic (-)-centolobine.
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