Total synthesis of (−)-mniopetal F, a novel inhibitor of RNA-directed DNA-polymerases

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-...

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Bibliographic Details
Published in:Tetrahedron 2001-08, Vol.57 (34), p.7291-7301
Main Authors: Suzuki, Yoshikazu, Ohara, Aiko, Sugaya, Kenji, Takao, Ken-ichi, Tadano, Kin-ichi
Format: Article
Language:English
Subjects:
biologically active compounds
Diels–Alder reactions
Katsuki–Sharpless reactions
terpenes and terpenoids
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Summary: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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)00686-X