Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2010(3): 0354-0354
DOI: 10.1055/s-0029-1219418
DOI: 10.1055/s-0029-1219418
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Michael Addition for the Synthesis of Octahydroindole Natural Products
S. V. Pansare*, R. Lingampally, R. L. Kirby
Memorial University, St. John’s, Canada
Further Information
Publication History
Publication Date:
18 February 2010 (online)
![](https://www.thieme-connect.de/media/synfacts/201003/lookinside/thumbnails/10.1055-s-0029-1219418-1.jpg)
Significance
Pansare and co-workers report an enantioselective route toward the aryloctahydroindole core of several natural products. Their approach is based on the highly enantio- and diastereoselective Michael addition between ketones 1 and nitroalkenes 2 using the triamine salt catalyst 3. The resulting γ-nitro ketone 4a was diastereoselectively transformed into the cis-octahydro-indole 7 in five steps. This intermediate was further functionalized to tetracycle 8, thus completing a formal synthesis of (-)-pancracine.