C-2 primary alcohols

Reduction of the resulting primary alcohols 150 to 153 over palladium black proved to be a relatively slow process at atmospheric pressure, the reactions requiring up to 2 days to reach completion, but most importantly, good yields were obtained accompanied by complete stereocontrol. Only the products 154 to 157 with the correct kainoid C-3/C-4 cis relative stereochemistry were obtained (Scheme 58 and Table 14). The C-2 primary alcohol functionality appeared to be responsible for this... 

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