LiHMDS tetrahydrofuran → HCID 69957539, compound

Participants

Reaction Steps

Similarly to Example 3, 1.35 g(6.07 mmol) of (3R,3aR,4S,4aR,8aS,9R,9aS)-4,9-epoxy-3-methyl-decahydronaphtho[2,3-c]furan-1(3H)-one were reacted with 27.6 mg(5 equivalents) of lithium bis(trimethylsilyl)amide-tetrahydrofuran solution(1.1M) to obtain 1.37 g of (3R,3aR,4S,4aR,8aS)-4-hydroxy-3-methyl-3a,4,4a,5,6,7,8,8a-octahydronaphtho[2,3-c]furan-1(3H)-one and then reacted with 4.54 ml(5 equivalents) of 1,8-diazabicyclo[5.4.0]undec-7-ene to obtain 1.05 g of (3R,3aR,4S,4aR,9aR)-4-hydroxy-3-methyl-3a,4,4a,5,6,7,8,9a-octahydronaphtho[2,3-c]furan-1(3H)-one(yield after 2 processes 78%).

Provenance & Evidence