How would you synthesise tetrahydrohyperforin and octahydrohyperforin from hyperforin?

Question

The chemical structure of the compounds in question are:

Figure 1: Hyperforin

Figure 2: Tetrahydrohyperforin

Figure 3: Octahydrohyperforin

Would heating hyperforin in the presence of water manage to saturate the required bonds and thus allow one to synthesise these compounds?

Answer 1

That route won't work.

You need a hard base reduction that does not attack the enone, or you need to protect the enone to make Tetrahydrohyperforin.

Catalytic hydrogenation that is selective against carbonyl reduction is necessary to make Octahydrohyperforin.