PURPOSE: To obtain the subject compound as a sex pheromone for exterminating Popillia japonica Newman by reacting D-ribose with acetone, reacting the resultant product with a Wittig reagent, converting only primary OH group of the product into a leaving group and then treating the prepared compound with a base, etc.
CONSTITUTION: D-Ribose expressed by formula I is reacted with acetone to provide a compound expressed by formula II, which is subsequently reacted with a Wittig reagent expressed by formula III to afford a compound expressed by formula TV. Only primary OH group in the resultant compound expressed by formula TV is then selectively converted into a leaving group -OL to afford a compound expressed by formula V, which is subsequently treated with a base. The resultant product is then reacted with an acetic acid equivalent in the presence of a basic catalyst to afford a product, which is subsequently lactonized to provide a compound expressed by formula VI (R is α-substituent group of the acetic acid equivalent). The obtained compound is then catalytically hydrogenated and treated with an acid to hydrolyze the ketal part. Thereby, a compound expressed by formula VII is obtained and reacted with an orthoformic acid ester. The prepared product is reductively released to afford the objective compound expressed by formula VIII.
| WO/1997/017333 | BENZOXAZINE ANTIMICROBIAL AGENTS |
| JP2007039389 | METHOD FOR PRODUCING L-ARABONO-γ-LACTONE CRYSTAL |
KAWAKAMI HIROSHI
KOSEKI YUKIFUMI
MATSUSHITA HAJIME
ONO MIKIO
FUJI FLAVOR CO