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A new route to seven-and eight-membered carbocycles

✍ Scribed by Jong Sun U; Jinhwa Lee; Jin Kun Cha

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
227 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

A facile method for the construction of bicyclo[6.3.0]undecane or bicyclo-[5.3.0]decane skeleton has been developed by the tandem application of the intramolecular Kulinkovich cyclopropanation of co-vinyl esters and oxidation of the resulting cyclopropanols.

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Highly diastereoselective thermal [5C2C] intramolecular pyrone Β± alkene cycloadditions can be achieved by introducing a homochiral ptolylsulfinyl group at a suitable position of the alkene. The resulting adducts can be readily desulfinylated to give optically active 8-oxabicyclo[3.2.1]octane derivat