Aminosugar-based immunomodulator lipid A: synthetic approaches

• Alla Zamyatina

Beilstein J. Org. Chem. 2018, 14, 25–53, doi:10.3762/bjoc.14.3

Oxidative dehydrogenation of C–C and C–N bonds: A convenient approach to access diverse (dihydro)heteroaromatic compounds

• Santanu Hati,
• Ulrike Holzgrabe and
• Subhabrata Sen

Beilstein J. Org. Chem. 2017, 13, 1670–1692, doi:10.3762/bjoc.13.162

• catalytic amount of potassium iodide (0.2 mmol) and 0.25 mL of tert-butylhydroperoxide (TBHP, 70 wt %) in water (4 equiv) to afford the dihydroisoquinazoline 34a, which got oxidized to the quinazolium intermediate 34b. Hydroxylation of 34b afforded 34c, which was further reacted with nitroalkanes at 50 °C

Stereoselective synthesis of hernandulcin, peroxylippidulcine A, lippidulcines A, B and C and taste evaluation

• Marco G. Rigamonti and
• Francesco G. Gatti

Beilstein J. Org. Chem. 2015, 11, 2117–2124, doi:10.3762/bjoc.11.228

• epoxidation of 5 with tert-butylhydroperoxide (TBHP) in toluene gave 6 ([α]D +34.2° (c 1.3, CHCl3)) in 95% yield [9][22]. Then, the diol 7 was obtained in 85% yield from the reduction of epoxide 6 with LiAlH4 in THF at 0 °C. The diol 7 was easily purified by crystallization (85% yield, n-hexane at −50 °C up

Exploration of C–H and N–H-bond functionalization towards 1-(1,2-diarylindol-3-yl)tetrahydroisoquinolines

• Michael Ghobrial,
• Marko D. Mihovilovic and
• Michael Schnürch

Beilstein J. Org. Chem. 2014, 10, 2186–2199, doi:10.3762/bjoc.10.226

• functionalized indoles into position 1 of N-arylated THIQ in presence of tert-butylhydroperoxide (t-BHP) using copper(I) bromide as catalyst (Scheme 1) [15]. Inspired by this report the method has been expanded by others in terms of oxidant, catalyst and substrate scope [16][17][18][19][20][21]. In our group we

Silver and gold-catalyzed multicomponent reactions

• Giorgio Abbiati and
• Elisabetta Rossi

Beilstein J. Org. Chem. 2014, 10, 481–513, doi:10.3762/bjoc.10.46

Synthesis and biological activity of N-substituted-tetrahydro-γ-carbolines containing peptide residues

• Nadezhda V. Sokolova,
• Valentine G. Nenajdenko,
• Vladimir B. Sokolov,
• Daria V. Vinogradova,
• Elena F. Shevtsova,
• Ludmila G. Dubova and
• Sergey O. Bachurin

Beilstein J. Org. Chem. 2014, 10, 155–162, doi:10.3762/bjoc.10.13

• previously described [23]. All experiments were provided with mitochondria energized by succinate in the presence of rotenone. The influence of compounds on spontaneous or induced by tert-butylhydroperoxide (t-BHP) LP was studied by the standard assay [24]. The extent of LP was measured

Selective copper(II) acetate and potassium iodide catalyzed oxidation of aminals to dihydroquinazoline and quinazolinone alkaloids

• Matthew T. Richers,
• Chenfei Zhao and
• Daniel Seidel

Beilstein J. Org. Chem. 2013, 9, 1194–1201, doi:10.3762/bjoc.9.135

• Matthew T. Richers Chenfei Zhao Daniel Seidel Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA 10.3762/bjoc.9.135 Abstract Copper(II) acetate/acetic acid/O2 and potassium iodide/tert-butylhydroperoxide systems are shown

• to affect the selective oxidation of ring-fused aminals to dihydroquinazolines and quinazolinones, respectively. These methods enable the facile preparation of a number of quinazoline alkaloid natural products and their analogues. Keywords: aminal; copper; oxygen; tert-butylhydroperoxide

• tetrahydroquinazoline aminals are converted to quinazolinones using tert-butylhydroperoxide (TBHP) and catalytic potassium iodide [36][37]. While these examples deal with the oxidation of bicyclic aminals, we were interested in developing methods to create dihydroquinazoline and quinazolinone alkaloids from ring-fused