Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 6, Pages 3537-3551Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b03141
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Funding
- SERB New Delhi [EMR/2017/000499]
- University Grants Commission of India (UGC)
- Council of Scientific and Industrial Research (CSIR), New Delhi
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A metal-free, Bronsted acid, pTsOH-catalyzed intramolecular rearrangement of delta-hydroxyalkynones to substituted 2,3-dihydro-4H-pyran-4-ones was developed. The rearrangement occurs with high regioselectivity under mild and open-air conditions. The scope of work was illustrated by synthesizing an array of aliphatic and aromatic substituted 2,3-dihydro-4H-pyran-4-ones in up to 96% yield, 100% atom economy, and complete regioselectivity. Some of the dihydropyranones are utilized for vinylic halogenations and to complete the total synthesis of bioactive natural products, obolactone and a catechol pyran isolated from Plectranthus sylvestris (Labiatae).
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