The bicyclo[4,2,1]nonanols (II; R1= H, R2= OH; R1= OH, R2= H) are obtained by reduction of the lactone (I) with lithium hydrido-t-butoxyaluminate, and dehydrochlorination of the chloride (II; R1= H, R2= Cl) with collidine affords the bridgehead olefin (V).
W. Carruthers and M. I. Qureshi, J. Chem. Soc. D, 1969, 832b DOI: 10.1039/C2969000832B
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