NOVEL 10-MEMBERED CYCLIC COMPOUND AND PRODUCTION THEREOF

摘要

NEW MATERIAL:The compound of formula I [R1 is H or OH-protecting group; Z is direct bond or O constituting oxirane ring having the configuration of (2,3-cis-5R*, 8S*) or (2R*, 3R*, 5R*, 8S*]. EXAMPLE:4-Isopropyl-7-hydroxymethyl-9,10-epoxy-5-cyclodecen-1-one. USE:An inexpensive raw material for the synthesis of periplanone-B of formula II which is sex hormone of Periplaneta americana (a kind of cockroach). PREPARATION:The compound of formula I wherein Z is direct bond can be produced by reacting the compound of formula III (R2 is protecting group of OH of alpha-cyanohydrin; A is eliminable group) with a base, and treating the product successively with an acid and then with a base. A compound of formula I wherein Z is other than direct bond is obtained by the position-specific and stereoselective epoxidization reaction of the alpha,beta-double bond of the carbonyl group of the above compound. When R1 of the compound of formula I is OH- protecting group, hydrolysis of the compound gives a compound of formula I wherein R1 is H.