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Total Synthesis of (±)-Longifolene
In 1954, Johnson and co-workers presented a total synthesis of the tricyclic sesquiterpene (±)-longifolene featuring an elegant formal [3+2] cycloaddition that provided fast access to the natural product.
Enyne G was accessed in four steps from enone A with an overall yield of 59%. Key cycloaddition of G efficiently provided the carbon skeleton of the natural product in 75% yield. Further elaboration of this intermediate afforded (±)-longifolene in four steps.
18 March 2021 (online)
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