Total synthesis of (R,R)-crinan via regiospecific and stereoselective palladium catalysed cyclisation

Article abstract of DOI:10.1016/S0040-4020(01)81882-2

The synthesis of (R,R)-crinan from (S)-1-cyclohexenylethan-1-ol is described. The key palladium catalysed step involves a regiospecific 6-exo trig cyclisation which proceeds with 20:1 stereoselectivity for the trans-ring junction over the cis-ring fusion. The ring junction stereochemistry is sensitive to solvent, phosphine and small amounts of water.