Bisnorisocomene

Since our direct route to angularly fused triquinanes from cycloaddition of l-(4-pentynyl)cyclopen-tenes is limited to trisubstituted alkenes and simple terminal alkynes, bisnorisocomene, but not iso-comene itself, could be prepared (Scheme 22). However, this limitation is not a factor for most other compounds in this class of natural products, and the steric interactions described earlier worked to our advantage in a diastereocontrolled synthesis of pentalenene (see structure. Scheme 20). The natural product was obtained by subjecting the product of Scheme 14 to the sequence i, Li, NH3, MeOH ii, MeLi, Et20 iii, p-TsOH, benzene, reflux. ... 

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