Bulletin of the Chemical Society of Japan p. 3931 - 3932 (1982)
Update date:2022-08-03
Topics:
Yoshida, Takashi
Saito, Shojiro
cis-Jasmone was efficiently synthesized from 2-cyclopentenone.The treatment of cyclopentenone with sodium p-toluenesulfinate gave 3-(p-tolylsulfonyl)cyclopentanone in a 92.5percent yield.The alkylation of the sulfone, after the protection of the ketone, with cis-1-bromo-3-hexene, followed by desulfonylation with 5percent hydrochloric acid in tetrahydrofuran, afforded 3-(cis-3-hexenyl)-2-cyclopentenone in a good yield.The retroaldol-aldol condensation of the cyclopentenone in a stainless steel autoclave in presence of 5percent sodium hydroxide yielded cis-jasmone in a 80percent yield.
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