The first total syntheses of alkaloids phleghenrines A and C have been accomplished in 19 and 18 steps, respectively, relying on three (hetero)-Diels-Alder ([4 + 2]) cycloaddition reactions to forge the cyclic molecular backbone and two ring-expansion reactions to manipulate the ring size. A chiral precursor is synthesized through an auxiliary controlled Diels-Alder reaction, rendering the asymmetric synthesis accessible. The established strategy provides a general approach to the relevant novel alkaloids.
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| http://dx.doi.org/10.1021/acs.orglett.3c00755 | DOI Listing |
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