AI Article Synopsis
- - Progress is being made toward a unified method for creating the alkaloid jervine using two main fragments made from cost-effective and widely available materials.
- - Critical reactions in this synthesis include a highly selective Ireland-Claisen rearrangement that connects the amine and methyl group, and a selective selenoetherification that forms a specific configuration of a complex molecule.
- - Additionally, an enzymatic process is used to convert an abundant, non-chiral diol into an essential four-carbon component, providing an efficient alternative to a traditional method involving a protected Roche ester reduction.
Article Abstract
Progress toward a convergent approach for the enantioselective synthesis of the alkaloid jervine is presented. The two requisite fragments were stereoselectively and efficiently fashioned from economical and readily available reagents. Key reactions include (a) a highly diastereoselective Ireland-Claisen rearrangement to establish the necessary relationship between the amine and methyl group on the tetrahydrofuran E-ring; (b) a diastereoselective selenoetherification reaction that enabled the assembly of the D/E oxaspiro[4.5]decene in the needed configuration; and (c) an enzymatic desymmetrization of an abundant achiral diol en route to a key four-carbon building block as a practical alternative to a protected Roche ester reduction.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7212305 | PMC |
| http://dx.doi.org/10.1021/acs.orglett.0c00972 | DOI Listing |
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