Abstract
The asymmetric total synthesis of (–)-rossinone A, a meroterpene exhibiting a range of pharmacologically important biological activities, has been accomplished for the first time from geraniol by a concise eight-step sequence that involves the Horner–Wadsworth–Emmons reaction of an aldehyde derived from a geranylated hydroquinone intermediate with a chiral phosphonate prepared via the highly diastereoselective Davis oxidation of a known oxazolidinone derivative.
Original language | English |
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Article number | 153456 |
Journal | Tetrahedron Letters |
Volume | 84 |
DOIs | |
Publication status | Published - 2021 Nov 9 |
Keywords
- Davis oxidation
- Horner–Wadsworth–Emmons reaction
- Meroterpene
- Rossinone
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry