155392-68-0

Upstream product

• 100348-93-4 (R)-Wieland-Miescher ketone 
• 50-00-0 formaldehyd 
• 108-98-5 thiophenol 
• 117556-90-8 (8aR)-3,4,8,8a-tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione 1-ethylene ketal 

Relevant academic research and scientific papers

Synthesis of manool-related labdane diterpenes as platelet aggregation inhibitors

Enantioselective total synthesis of the labdane diterpene (-)-1, was achieved starting from the R-(-)-enantiomer of the Wieland-Miescher ketone (3). The enantiomer (+)-1 was obtained by partial synthesis via microbial transformation of sclareol (24). These results established that the natural compound (+)-1, a platelet aggregation inhibitor, has a normal absolute stereochemistry like that of manool (2). The B-norlabdane-related compound 44 was also synthesized using a novel ring contraction reaction.

Large-scale preparation of enantiomerically pure (4aR)-(-)-1,4a-dimethyl-4, 4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione: A useful Wieland-Miescher diketone analogue

Wieland-Miescher diketone analogue 1 is a widely used precursor for asymmetric synthesis of natural sesquiterpenes and diterpenes. We describe here a large-scale preparation (>125 g batches) of enantiomerically pure compound 1 starting from propionyl chloride and using very simple and cheap reagents. A new one-pot sequence to the intermediate 2-methylcyclohexane-1,3-dione is also described. Georg Thieme Verlag Stuttgart.