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Synfacts 2021; 17(04): 0373
DOI: 10.1055/s-0040-1719436
DOI: 10.1055/s-0040-1719436
Synthesis of Natural Products and Potential Drugs
Total Synthesis of (±)-Longifolene
Volkmann RA,
Andrews GC,
Johnson WS.
Stanford University, USA
Novel Synthesis of Longifolene.
J. Am. Chem. Soc. 1975;
97: 4777-4779
DOI: 10.1021/ja00849a062
Novel Synthesis of Longifolene.
J. Am. Chem. Soc. 1975;
97: 4777-4779
DOI: 10.1021/ja00849a062
Significance
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.
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Comment
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.
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Publication History
Article published online:
18 March 2021
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