Pinocarveol synthesis

Myrtenol (203 X = CH2OH) may be obtained most efficiently from the more stable secondary allylic alcohol (+)-trans-pinocarveol (30 enantiomer) via bromination with PBra to the rearranged bromide (203 X = CH2Br) [(30) (203 X = CH20H)/85 15] ester thermolysis and isomerization-oxidation were less effective, and the direct acid-catalysed isomerization was not observed. Intramolecular cyclization of (206), which is readily synthesized via trifluoroacetic anhydride cyclization of 4-methylcyclohex-3-enylacetic acid to (186), affords (207) which is cleaved to (208 X = NH2) in a synthesis of ( )-a-... 

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