Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2019, Issue 24, Pages 3916-3920Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201900610
Keywords
Medium-ring compounds; Synthetic methods; Cyclization; Catalysis; Indole
Categories
Funding
- Japan Society for the Promotion of Science (JSPS) KAKENHI [16K08154, 19K06991, 17J03524, 17H03969]
- Tokyo Biochemical Research Foundation [16-B1-5]
- Institute for Global Prominent Research, Chiba University
- Grants-in-Aid for Scientific Research [19K06991, 16K08154, 17H03969, 17J03524] Funding Source: KAKEN
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A new approach to cycloocta[b]indole through formal [5+3] cycloaddition was developed. This methodology was realized by using an indole derivative as a C5 unit and a cyclopropane derivative as a C3 unit. These two units have both donor and acceptor properties. Two carbon-carbon bonds were formed stepwise by the successive addition of a Lewis acidic catalyst and a Bronsted base. The reaction could be performed as a one-pot process. Optically active cycloocta[b]indole was also synthesized by using this methodology with a chiral cyclopropane as a C3 substrate.
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