75445-60-2Relevant academic research and scientific papers
A regioselective synthesis of 7-methyl juglone and its derivatives
Cui, Jiahua,Li, Shaoshun,Jia, Jinping
, p. 18 - 25 (2020/05/14)
7-Methyl juglone as a naturally occurring naphthoquinone showed striking antibacterial, antifungal, antivirus and anticancer activity. Its derivatives had also been characterized as key intermediates in the preparation of natural naphthoquinones and anthraquinones. Herein, we reported a regioselective synthesis of 7-methyl juglone via the construction of fused polycyclic systems. The key steps of the strategy involved Stobbe condensation of 2,5-dimethoxy benzaldehyde with diethyl succinate, intramolecular cyclization, reduction, acid-facilitated debenzylation and further cerium(IV) ammonium nitrate-mediated oxidation. Compared with the reported methods employing Birch conditions in liquid ammonia or Friedel-Crafts cycloacylation with melting heat of aluminum salts, the reaction conditions in the new synthetic route were milder and suitable for large scale preparations. In addition, all of the starting materials in the synthesis were readily available. It has great implications for the design and synthesis of structurally asymmetric naphthoquinones derivatives.
Studies toward the syntheses of pluramycin natural products. the first total synthesis of isokidamycin
O'Keefe, B. Michael,Mans, Douglas M.,Kaelin Jr., David E.,Martin, Stephen F.
experimental part, p. 6524 - 6538 (2011/09/20)
We report the first total synthesis of the complex C-aryl glycoside isokidamycin, the epimer of the naturally-occurring pluramycin antibiotic kidamycin. The synthesis features a highly efficient Diels-Alder reaction between a substituted naphthyne and a glycosylated furan to form the anthracene core bearing a pendent angolosamine C-glycoside. The regiochemical outcome of the Diels-Alder reaction was controlled by employing a disposable silicon tether to link the reactive naphthyne and the glycosyl furan, rendering the cycloaddition intramolecular. The benzopyranone moiety of the aromatic nucleus was appended by cyclization of a functionalized vinylogous amide onto an advanced anthrol intermediate. The vancosamine amino glycoside was introduced by an O→C-glycoside rearrangement that produced the β-anomer. Subsequent refunctionalizations then led to isokidamycin.
Total synthesis of isokidamycin
O'Keefe, B. Michael,Mans, Douglas M.,Kaelin Jr., David E.,Martin, Stephen F.
scheme or table, p. 15528 - 15530 (2011/01/12)
The synthesis of isokidamycin, which represents the first total synthesis of a bis-C-aryl glycoside natural product in the pluramycin family, has been completed. The synthesis features the use of a silicon tether as a disposable regiocontrol element in an intramolecular Diels-Alder reaction between a substituted naphthyne and a glycosyl furan and a subsequent O→C-glycoside rearrangement.
Dimeric Naphthoquinones, IV1). - Synthesis of Biramentaceone, Mamegakinone and Rotundiquinone
Laatsch, Hartmut
, p. 1321 - 1347 (2007/10/02)
Mamegakinone (8a), biramentaceone (12a), 3,3'-bijuglone (8b), 2,2-bijuglone (12b) and their methyl ethers were prepared by oxidative coupling of substituted 4-methoxy-1-naphthols; indigoids like 24 are intermediates.Cooxidation of the isomeric dimethoxy-1
