Abstract
The enantioselective total synthesis of an unusual pentacyclic proaporphine alkaloid, (-)-misramine, was achieved. The synthetic strategy relied on an enantioselective intramolecular Friedel-Crafts-type 1,4-addition using an asymmetric organocatalyst to construct a spiroindane skeleton containing an all-carbon quaternary stereocenter and a double reductive amination of the keto-aldehyde to form a piperidine ring toward the end of the synthesis. This work is the first example of asymmetric synthesis of a proaporphine alkaloid.
| Original language | English |
|---|---|
| Pages (from-to) | 5044-5047 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 20 |
| Issue number | 16 |
| DOIs | |
| Publication status | Published - 2018 Aug 17 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Cite this
Yoshida, K., Fujino, Y., Takamatsu, Y., Matsui, K., Ogura, A., Fukami, Y., Kitagaki, S., & Takao, K-I. (2018). Enantioselective Total Synthesis of (-)-Misramine. Organic Letters, 20(16), 5044-5047. https://doi.org/10.1021/acs.orglett.8b02198