Abstract
The total syntheses of eight members of the palmarumycin family have been achieved, with identification of the absolute stereochemistry for three of these natural products. In addition, the ras-farnesyl transferase inhibitor (-)-preussomerin G has been synthesized, achieving the first enantioselective route for accessing this family of natural products. Highlights of the synthetic work include an asymmetric epoxidation of a cyclic enone in excellent yield and enantiomeric excess and a potentially biomimetic oxidative spirocyclization for the introduction of the bis-spiroketal array unique to the preussomerin natural products.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Biological Products / chemical synthesis*
-
Biological Products / chemistry
-
Catalysis
-
Chromatography, High Pressure Liquid
-
Combinatorial Chemistry Techniques / methods*
-
Cyclization
-
Dioxanes / chemical synthesis*
-
Enzyme Inhibitors / chemical synthesis*
-
Epoxy Compounds
-
Fungi / chemistry
-
Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
-
Magnetic Resonance Spectroscopy
-
Molecular Conformation
-
Molecular Structure
-
Naphthalenes / chemical synthesis
-
Naphthalenes / chemistry
-
Spiro Compounds / chemical synthesis*
-
Stereoisomerism
Substances
-
Biological Products
-
Dioxanes
-
Enzyme Inhibitors
-
Epoxy Compounds
-
Heterocyclic Compounds, 4 or More Rings
-
Naphthalenes
-
Spiro Compounds
-
palmarumycin C12
-
palmarumycin C2
-
palmarumycin CP2
-
preussomerin G
-
palmarumycin CP(1)