Synfacts 2021; 17(04): 0373
DOI: 10.1055/s-0040-1719436
Synthesis of Natural Products and Potential Drugs

Total Synthesis of (±)-Longifolene

Contributor(s):
Erick M. Carreira
,
Hendrik Bulthaupt
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.
 

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

Publication Date:
18 March 2021 (online)

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