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A formal total synthesis of the sesquiterpene (±)-herbertenediol and its dimers mastigophorenes A–D has been accomplished, starting from vanillin via 2,3-dimethoxy-5-methylbenzaldehyde. A combination of Claisen rearrangement and ring-closing metathesis reactions were employed for the generation of the two vicinal quaternary carbons on a cyclopentane ring.
Efficient total syntheses of the herbertane sesquiterpene title compounds have been accomplished employing an Ireland ester Claisen rearrangement and ring-closing metathesis reaction sequence based strategy for the construction of two stereogenic vicinal quaternary carbon atoms on a cyclopentane.
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