551939-58-3Relevant academic research and scientific papers
Tandem intramolecular benzyne-furan cycloadditions. Total synthesis of vineomycinone B2 methyl ester
Sparks, Steven M.,Chen, Chi-Li,Martin, Stephen F.
, p. 8619 - 8635 (2008/02/08)
We have exploited tandem intramolecular benzyne-furan cycloadditions employing three different benzyne precursors to generate substituted bisoxabenzonorbornadienes in a single operation. The regiochemical outcomes in these Diels-Alder reactions were effectively controlled by using disposable silicon tethers to link the reacting benzyne and furan moieties. Two different methods for converting the intermediate bisoxabenzonorbornadienes to substituted anthrarufins were developed. The first tactic entails the initial cleavage of the silicon tethers followed by regioselective ring opening of the oxabicycloheptadienes and oxidation of the central ring giving the target anthrarufin, whereas the second features the regioselective ring opening of the oxabicycloheptadienes followed by protiodesilylation and oxidation. When the starting furans bear carbohydrate substitutents, this new methodology enables the rapid assembly of the glycosyl-substituted aromatic cores of complex C-aryl glycoside antibiotics from simple starting materials. The utility of this novel approach to anthrarufins and C-aryl glycosides is exemplified in a triply convergent synthesis of vineomycinone B2 methyl ester.
C-aryl glycosides via tandem intramolecular benzyne-furan cycloadditions. Total synthesis of vineomycinone B2 methyl ester
Chen, Chi-Li,Sparks, Steven M.,Martin, Stephen F.
, p. 13696 - 13697 (2007/10/03)
A triply convergent total synthesis of vineomycinone B2 methyl ester has been achieved by an approach with a longest linear sequence of 16 steps. The synthesis features the use of silicon tethers as disposable linkers to control the regiochemis
General entries to C-aryl glycosides. Formal synthesis of galtamycinone
Apsel, Beth,Bender, John A.,Escobar, Maya,Kaelin Jr., David E.,Lopez, Omar D.,Martin, Stephen F.
, p. 1075 - 1077 (2007/10/03)
Utilizing a general entry we had developed for the synthesis of C-aryl glycosides, we have prepared the juglone derivatives 18-20 as well as the juglone precursor 13. Because 19 had been previously converted in two steps by Suzuki into galtamycinone (1), its preparation constitutes a total synthesis of 1.
