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Synfacts 2020; 16(11): 1257
DOI: 10.1055/s-0040-1706316
Synthesis of Natural Products and Potential Drugs

Total Synthesis of (±)-Aspidofractinine

Contributor(s):
Erick M. Carreira
,
Fabian Glatz
Wang S.-H, Si R.-Q, Zhuang Q.-B, Guo X, Ke T, Zhang X.-M, *, Zhang F.-M, *, Tu Y.-Q. * Lanzhou University and Shanghai Jiao Tong University, P. R. of China
Collective Total Synthesis of Aspidofractinine Alkaloids through the Development of a Bischler–Napieralski/Semipinacol Rearrangement Reaction.

Angew. Chem. Int. Ed. 2020;
DOI: 10.1002/anie.202009238
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Key words

(±)-aspidofractinine - Bischler–Napieralski reaction - semipinacol rearrangment - Mannich reaction

Significance

The authors report the total synthesis of (±)-aspidofractinine employing a Bischler–Napieralski/semipinacol sequence as key step. In combination with a Mannich reaction, four aspidofractinine alkaloids were synthesized, all containing a bicyclo[2.2.2]octane framework.


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Comment

Treatment of formamide D with Tf2O triggered the Bischler–Napieralski/semipinacol cascade furnishing hemiacetal F, which underwent a Mannich reaction to give ketone G. Ring expansion followed by glycol-cleavage and aldol condensation led to enone N, which was transformed to the natural product after functional group interconversions.


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Publication History

Article published online:
20 October 2020

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