To obtain the subject new compound having osteogenesis promoting activity.
This new compound is shown by formula I [R1 is a halogen, etc.; R2 is a group of the formula (CH2)qY2rR5 (Y2 is O, etc.; R5 is H, etc.; (r) is 0 or 1; (q) is 0-5); X is H, etc.; Z is ethylene, etc.], e.g. 6,7-dinol-5,8-inter- o-phenylene-PGA1. The compound of formula I is obtained by the following process: furan is lithiated and then reacted with a compound of formula II (R6 is a halogen, etc.), to form a compound, which is then rearranged, isomerized in the presence of an acid or base catalyst, and subjected to OH group protecting to form a compound of formula III (R7 is an OH-protecting group), which, in turn, is reacted with an organic borane compound corresponding to R1 in the presence of a base and a Pd catalyst to form a compound, which is then reacted with a compound prepared by reaction of an organolithium reagent with e.g. copper iodide, and the hydroxyl group of the resulting compound of formula IV (X2 is H, etc.), is deprotected, followed by conducting a dehydration.
SHIMAZAKI YOICHI
ONO NAOYA
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