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A Total Synthesis of Paeoveitol.
- Source :
-
Organic Letters . Aug2016, Vol. 18 Issue 15, p3698-3701. 4p. - Publication Year :
- 2016
-
Abstract
- 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 π-π stacking interaction that govern selectivity in this process. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 15237060
- Volume :
- 18
- Issue :
- 15
- Database :
- Academic Search Index
- Journal :
- Organic Letters
- Publication Type :
- Academic Journal
- Accession number :
- 117301014
- Full Text :
- https://doi.org/10.1021/acs.orglett.6b01736