Asymmetric Total Syntheses of (+)‐Mycoepoxydiene (IV) and Related Natural Product (‐)‐1893A (V): Application of One‐Pot Ring‐Opening/Cross/Ring‐Closing Metathesis to Construct Their 9‐Oxabicyclo[4.2.1]nona‐2,4‐diene Skeleton.
pmid: 15575759
Asymmetric Total Syntheses of (+)‐Mycoepoxydiene (IV) and Related Natural Product (‐)‐1893A (V): Application of One‐Pot Ring‐Opening/Cross/Ring‐Closing Metathesis to Construct Their 9‐Oxabicyclo[4.2.1]nona‐2,4‐diene Skeleton.
The total syntheses of (+)-mycoepoxydiene and (-)-1893A have been completed. The present synthetic strategy features the use of one-pot ring-opening/cross metathesis (ROM/CM) followed by a ring-closing metathesis (RCM) reaction, allowing for the concise construction of the 9-oxabicyclo[4.2.1]nona-2,4-diene framework from a 7-oxabicyclo[2.2.1]hept-2-ene derivative and 1,3-butadiene. The sequential metathesis product was converted into (+)-mycoepoxydiene through the oxidative rearrangement of a furfuryl alcohol to a pyranone, thereby establishing its absolute stereochemistry. From the common intermediate, a structurally related natural product (-)-1893A was also synthesized via the vinylogous aldol reaction.
- Keio University Japan
Bridged-Ring Compounds, Pyrones, Molecular Conformation, Cycloparaffins
Bridged-Ring Compounds, Pyrones, Molecular Conformation, Cycloparaffins
15 Research products, page 1 of 2
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