4.8 Article

Total syntheses of sesterpenic acids:: Refuted (±)-bilosespenes A and B

Journal

ORGANIC LETTERS
Volume 5, Issue 24, Pages 4741-4743

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol035944i

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The total syntheses of racemic sesterpenic acids 1 and 2 have been accomplished from creosol (6) in 12 and 13 steps, respectively. Intramolecular Diels-Alder reaction of masked o-benzoquinone 7 generated from 6 and allyl alcohol, stereoselective addition of alkenylcerium(III) chloride 8 to ketone 5, and anionic oxy-Cope rearrangement of dienol 4 are the key steps.

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