Journal
ORGANIC LETTERS
Volume 18, Issue 15, Pages 3698-3701Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b01736
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Funding
- National Science Foundation of China [21202074, 21473107]
- Shaanxi Provincial Natural Science Foundation [2016JQ2024]
- Fundamental Research Funds for the Central Universities [GK201603046]
- Shaanxi Normal University
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A four-step total synthesis of paeoveitol (1), a recently disclosed norditerpene natural product from Paeonia vetchii, is reported. This highly concise synthetic route was guided by biosynthetic considerations and enabled by an unusual intermolecular ortho-quinone methide [4 + 2]-cycloaddition reaction, which proceeded with excellent regio- and diastereoselectivity. Density functional theory (DFT) calculations point to a crucial intermolecular hydrogen bond and pi-pi stacking interaction that govern selectivity in this process.
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