Tetrahedron p. 3527 - 3533 (1982)
Update date:2022-08-03
Topics: Phenol Alkyl Experimental terms Alkenyl
Gill, Melvyn
Herlt, Anthony J.
Rickards, Rodney W.
An efficient and versatile synthesis of 3-alkyl- and 3-alkenyl-5-hydroxycyclopent-2-enones is described.The key intermediate, 4-(t-butyldimethylsilyloxy)-3-methoxycyclopent-2-enone (5), is prepared in five steps from phenol. 1,2-Addition of various organolithium and Grignard reagents yields tertiary alcohol intermediates which afford the title compounds after solvolysis and desilylation.
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