74262-56-9Relevant articles and documents
Structure–activity relationship study of the anti-obesity natural product yoshinone A
Kawazoe, Yoshinori,Itakura, Yuki,Inuzuka, Toshiyasu,Omura, Sachikazu,Uemura, Daisuke
, p. 226 - 232 (2021/03/06)
Yoshinone A was derived from marine algae and shown to inhibit adipogenic differentiation. The natural compound is composed of a γ-pyrone ring and a side chain and that contains two asymmetric carbons. Although their absolute configuration has been determ
Stereoselective Total Synthesis of (+)-Aristolactam GI
Luong, Tuan M.,Pilkington, Lisa I.,Barker, David
, p. 5747 - 5756 (2019/05/10)
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.
Total Synthesis and Structure Revision of Diplobifuranylone B
Cheng, Xinpeng,Quintanilla, Carlos D.,Zhang, Liming
, p. 11054 - 11060 (2019/09/12)
An asymmetric total synthesis of diplobifuranylone B was achieved in 10 steps for the longest linear sequence and in 15.8% overall yield from commercially available methyl (R)-(+)-lactate and l-glutamic acid. This synthesis features a stereoselective construction of the key 2,5-dihydrofuran ring in the natural product via a recently developed asymmetric gold catalysis. The stereochemical flexibility offered by the catalysis enables an expedient revision of the reported structure of diplobifuranylone B, where the relative stereochemistry of the 2,5-dihydrofuran moiety was previously misassigned as cis instead of trans.