Stereoselective Total Synthesis of (+)-Aristolactam GI.

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ID: 90155
2019
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Abstract
Aristolactams are an important subgroup of aporphinoids, which all share a common phenanthrene chromophore motif that is thought to be responsible for the range of interesting physicochemical and biological properties exhibited by these compounds. Among all of the aristolactams discovered, (+)-aristolactam GI displays a unique structural feature of having the aristolactam scaffold linked via a benzodioxane ring to a phenyl propanoid unit, resulting in the compound being an aporphinoid-lignan hybrid. The synthesis of (+)-aristolactam GI was achieved first by synthesis of an orthogonally protected aristolactam, which was prepared using a Suzuki/aldol cascade to convert a differentially protected isoindolin-1-one to the required phenanthrene. The required enantiopure phenyl propanoid unit was prepared from readily available ( R)-methyl lactate. A selective Mitsunobu reaction was used to combine these two key fragments, prior to the formation of the linking benzodioxane in the final step. The absolute stereochemistry of the natural product was confirmed to be 7' S, 8' S.
Reference Key
luong2019stereoselectivethe Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Luong, Tuan M;Pilkington, Lisa I;Barker, David;
Journal The Journal of organic chemistry
Year 2019
DOI
10.1021/acs.joc.9b00653
URL
Keywords
aristolochic acid upper tract urothelial carcinoma aristolochia species balkan endemic nephropathy aristolochic acid nephropathy

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