Article: Asymmetric Total Synthesis and Structure Elucidation of Huperzine H
Journal of organic chemistry. 2022 Jan. 18, v. 87, no. 5
2022
Abstract: A first asymmetric total synthesis of huperzine H has been achieved in a 12% overall yield from commercially available (+)-pulegone. The key steps of this synthesis include a highly diastereoselective Mukaiyama–Michael addition reaction of a pyrrole ... ...
| Abstract | A first asymmetric total synthesis of huperzine H has been achieved in a 12% overall yield from commercially available (+)-pulegone. The key steps of this synthesis include a highly diastereoselective Mukaiyama–Michael addition reaction of a pyrrole bearing a silyl enol ether and an intramolecular SN2 cyclization reaction with iodinated pyrrole acting as an effective nucleophile for the formation of the nine-membered ring. As a result, the relative and absolute stereochemistry of huperzine H is established. |
|---|---|
| Keywords | Lewis bases ; cyclization reactions ; diastereoselectivity ; organic chemistry ; pyrroles ; silyl enol ethers ; stereochemistry |
| Language | English |
| Dates of publication | 2022-0118 |
| Size | p. 3730-3735. |
| Publishing place | American Chemical Society |
| Document type | Article |
| ZDB-ID | 123490-0 |
| ISSN | 1520-6904 ; 0022-3263 |
| ISSN (online) | 1520-6904 |
| ISSN | 0022-3263 |
| DOI | 10.1021/acs.joc.1c02672 |
| Database | NAL-Catalogue (AGRICOLA) |
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