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Synfacts 2016; 12(10): 0999
DOI: 10.1055/s-0036-1589184
DOI: 10.1055/s-0036-1589184
Synthesis of Natural Products and Potential Drugs
Synthesis of (+)-Notoamides F, I, and R and (–)-Sclerotiamide
Further Information
Publication History
Publication Date:
19 September 2016 (online)
Key words
(+)-notoamide F - (+)-notoamide I - (+)-notoamide R - (–)-sclerotiamide - aza-Prins reaction - cobalt - radical cyclizationSignificance
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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