Abstract
We describe a simple chiral-pool synthesis of (-)-longamide B, (-)-longamide B methyl ester, and (-)-hanishin. The key feature of the total synthesis is the formation of a piperazinone from a 1,2-cyclic sulfamidate and methyl 2-pyrrolecarboxylate, which permits efficient construction of the pyrrolopiperazinone core scaffold.
| Original language | English |
|---|---|
| Article number | st-2015-u0727-l |
| Pages (from-to) | 616-620 |
| Number of pages | 5 |
| Journal | Synlett |
| Volume | 27 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - 2016 Mar 1 |
Keywords
- asymmetric synthesis
- hanishin
- heterocycles
- longamide B
- piperazinones
- sulfamidates
ASJC Scopus subject areas
- Organic Chemistry
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Shiokawa, Z., Inuki, S., Fukase, K., & Fujimoto, Y. (2016). Efficient Synthesis of (-)-Hanishin, (-)-Longamide B, and (-)-Longamide B Methyl Ester through Piperazinone Formation from 1,2-Cyclic Sulfamidates. Synlett, 27(4), 616-620. [st-2015-u0727-l]. https://doi.org/10.1055/s-0035-1560988