Abstract
We have achieved a total synthesis of (-)-mniopetal F, a drimane-type sesquiterpenoid which inhibits the reverse transcriptase activity of the human immunodeficiency virus (HIV)-1. The key step in our enantiospecific synthesis is a stereoselective intramolecular Diels-Alder reaction, in which the π-facial selectivity is controlled by the stereoelectronic effect of a trialkylsilyloxy substituent existing adjacent to the dienophile part.
Original language | English |
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Pages (from-to) | 7291-7301 |
Number of pages | 11 |
Journal | Tetrahedron |
Volume | 57 |
Issue number | 34 |
DOIs | |
Publication status | Published - 2001 Aug 20 |
Keywords
- Biologically active compounds
- Diels-Alder reactions
- Katsuki-Sharpless reactions
- Terpenes and terpenoids
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry