148679-92-9

Upstream product

• 148763-82-0 (1R,4S,6R)-6-hydroxy-1-methylbicyclo<2.2.2>octan-2-one 
• 148679-95-2 (1R,5S,7R)-4-allyl-7-(1-ethoxyethoxy)-1-methyl-2-oxabicyclo<3.2.1>nonan-3-one 
• 148679-94-1 (1R,5S,7R)-7-(1-ethoxyethoxy)-1-methyl-2-oxabicyclo<3.2.1>nonan-3-one 
• 148679-93-0 (1R,4S,6R)-6-(1-ethoxyethoxy)-1-methylbicyclo<2.2.2>octan-2-one 
• 129100-40-9 1R,4S,6S-6-hydroxy-1-methylbicyclo<2.2.2>octan-2-one 
• 98-59-9 p-toluenesulfonyl chloride 

Relevant academic research and scientific papers

Synthesis of mono- and sesquiterpenoids; XXII. Synthesis of (+)-pinthunamide, a sesquiterpene metabolite of a fungus, Ampulliferina sp.

Pinthunamide (1), a sesquiterpene metabolite produced by a fungus Ampliferina sp., was synthesized by starting from (1R,4S,6S)-6-hydroxy-1-methylbicyclo[2,2]octan-2-one (4), which could readily be prepared by yeast reduction of the corresponding β-diketone 5.

APPLICATION OF BIOCHEMICAL METHODS IN ENANTIOSELECTIVE SYNTHESIS OF BIOACTIVE NATURAL PRODUCTS

Enzymes as well as yeasts were used in enantioselective syntheses of bioregulators such as hormones and semiochemicals.Lipases and esterases were employed in achieving optical resolution, conversion of meso-compounds to optically active compounds, and macrolactonization.Lactase effected glucosidation of a phenolic hydroxy ketone without any protection of the functional groups.Yeasts provided a variety of optically active hydroxy esters and ketones, which served as versatile non-racemic chiral building blocks.