6-Methylhepta-3,5-dien-2-one → 4,8-Dimethylnon-7-EN-1-YN-4-OL

Participants

Reaction Steps

Reaction of this ketone with propargyl magnesium bromide provides 4,8-dimethyl-4-hydroxy-non-7-ene-1-yne. This alcohol is protected with trimethylsilyl chloride and converted to the trans vinyl tin derivative of 4,7-dimethyl-4-trimethylsiloxy-non-8-ene-1-yne which is converted to the corresponding prostagladin by the methods described in U.S. Pat. Nos. 4,322,543 and 4,271,314 to provide methyl 7-[3α-hydroxy-2β-(4-hydroxy-4,8-dimethyl-1,5,7-trans,trans,trans-nonatrienyl)-5-oxocyclopent ane]-1α-hept-4Z-enoate having the formula ##STR16##

Provenance & Evidence