HCID 69957837, compound → HCID 69957284, compound

Participants

Reaction Steps

Similarly to Referential example 4, 156.0 mg(0.35 mmol) of (2S,6R)-tert-butyl 2-[(E)-2-[(1R,3R,3aS,4S,4aR,8aS,9aR)-1-methoxy-3-methyl-dodecahydronaphtho[2,3-c]furan-4-yl]vinyl]-6-methyl-1-piperidinecarboxylate were reacted with 0.90 ml of Jones reagent to obtain 147.1 mg of (2S,6R)-tert-butyl 2-[(E)-2-[(3R,3aS,4S,4aR,8aS,9aR)-3-methyl-1-oxo-dodecahydronaphtho[2,3-c]furan-4-yl]vinyl]-6-methyl-1-piperidinecarboxylate, and then 1.00 ml of trifluoroacetic acid was reacted to obtain 113.0 mg of crude (3R,3aS,4S,4aR,8aS,9aR)-3-methyl-4-[(E)-2-[(2S,6R)-6-methylpiperidine-2-yl]vinyl]-3-methyl-decahydronaphtho[2,3-c]furan-1(3H)-one(yield after 2 processes 98%). Then, 0.30 ml of 37% formaldehyde solution and 47.1 mg (2.2 equivalents) of sodium cyanoboronhydride were reacted to obtain 100.8 mg of (3R,3aS,4S,4aR,8aS,9aR)-4-[(E)-2-[(2S,6R)-1.6-dimethylpiperidine-2-yl]vinyl]-3-methyl-decahydronaphtho[2,3-c]furan-1(3H)-one (ent-himbacine)(yield after 3 processes 84%).

Provenance & Evidence