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 |
|---|---|
| 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
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Cite this
Suzuki, Y., Ohara, A., Sugaya, K., Takao, K. I., & Tadano, K. I. (2001). Total synthesis of (-)-mniopetal F, a novel inhibitor of RNA-directed DNA-polymerases. Tetrahedron, 57(34), 7291-7301. https://doi.org/10.1016/S0040-4020(01)00686-X