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Synfacts 2016; 12(10): 0999
DOI: 10.1055/s-0036-1589184
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-Notoamides F, I, and R and (–)-Sclerotiamide

Contributor(s):
Erick M. Carreira
,
Marco Brandstätter
Zhang B, Zheng W, Wang X, Sun D, * Li C. * Shanghai Institute of Organic Chemistry and Ningbo University of Technology, P. R. of China
Total Synthesis of Notoamides F, I, and R and Sclerotiamide.

Angew. Chem. Int. Ed. 2016;
55: 10435-10438
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Publication History

Publication Date:
19 September 2016 (online)

 
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Key words

(+)-notoamide F - (+)-notoamide I - (+)-notoamide R - (–)-sclerotiamide - aza-Prins reaction - cobalt - radical cyclization

Significance

Herein, the authors describe the first total synthesis of (+)-notoamides F, I, and R, and (–)-sclerotiamide, isolated from the marine fungi Aspergillus sp. The synthetic strategy relies on a cobalt-mediated radical cycloisomerization and an aza-Prins cyclization to construct the bi­cyclo[2.2.2]diazaoctane core.


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Comment

Treatment of diamide D with FeCl3 induces an oxidative aza-Prins cyclization to give ester F in 67% yield. After Grignard addition of indole G, cobalt-mediated radical cyclization delivers K, which can be further transformed into (+)-notoamide I in three steps. From there, the other three natural products can be accessed.


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