Sodium borohydride → hexahydro-5-methyl-2H-cyclopenta[b]furan-2-one

Participants

Reaction Steps

The crude, optically active (3aR,4S,-5R,6aS)-[S*,R*(E)]-4-(4,4-dimethyl-1-oxo-2-octenyl)hexahydro-5-methyl-2H-cyclopenta[b]furan-2-one (11.1 g) was reduced with sodium borohydride (1.1 g) as described in Example V. After workup 10.45 g (93%) of optically active [3aR-[3aalpha,4alpha(1S*,2E),5beta,6aalpha]]-4-[1-(hydroxy)-4,4-dimethyl)-2-octenyl]hexahydro-5-methyl-2H-cyclopenta[b]furan-2-one was obtained as a viscous, amber colored oil. The product gave a single spot on TLC and was used as is in Examples XVI through XXIV of the synthesis.

Provenance & Evidence