2,5,5-Trimethyl-4-[(trimethylsilyl)oxy]cyclopent-2-en-1-one → HCID 54234765, compound

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Reaction Steps

The resulting 2,5,5-trimethyl-4-[(trimethylsilyl)oxyl]-cyclopent-2-en-1-one of formula VI is then condensed in a solvent (e.g. tetrahydrofuran) by means of a Grignard reaction with trimethyl-[(trans-3-methyl-pent-2-en-4-yn-1-yl)oxy]-silane of formula VII to give 5-[2,5,5-trimethyl-1-hydroxy-4-[(trimethylsilyl)oxy]-cyclopent-2-en-1-yl]-3-methyl-1-[(trimethylsilyl)oxy]-pent-2-en-4-yne of formula VIII which, without isolation, is saponified by shaking with a dilute aqueous alkali hydroxide solution to give 5-[1,4-dihydroxy-2,5,5-trimethyl-cyclopent-2-en-1-yl]-trans-3-methyl-pent-2-en-4-yn-1-ol of formula IX.

Provenance & Evidence