Selenium chlorides in the domino process of the regiospecific allyl chlorination of betulin and diacetylbetulin

References

• Hori T, Sharpless KB. Selenium-catalyzed nonradical chlorination of olefins with N-chlorosuccinimide. J Org Chem. 1979;44:4204–4208.
   Web of Science ®Google Scholar
• Ortgies S, Breder A. Oxidative alkene functionalizations via selenium-π-acid catalysis. ACS Catal. 2017;7:5828–5840.
   Web of Science ®Google Scholar
• Tietze LF, Branche G, Gerike KM. Domino reactions in organic synthesis. Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA; 2006.
   Google Scholar
• Guindon Y, Houde K, Prévost M, et al. Synthesis of propionate motifs: diastereoselective tandem reactions involving anionic and free radical based processes. J Am Chem Soc. 2001;123:8496–8501.
   PubMed Web of Science ®Google Scholar
• Amosova SV, Rykunova YI, Filippov AS, et al. Cascade regio- and stereoselective reactions of 2-bromomethyl-1,3-thiaselenole with water and ethylene glycol: en roote to the first representatives of polyfunctional 2,3-dihydro-1,4-thiaselenines. J Organomet Chem. 2018;867:398–403.
   Web of Science ®Google Scholar
• Potapov VA, Musalov MV, Musalova MV, et al. Stereoselective synthesis of E-2-halovinil tellanes, ditellanis and selenides based on tellurium tetrahalides, selenium dihalides and internal alkynes. J. Organomet. Chem. 2018;867:300–305.
   Web of Science ®Google Scholar
• Kurskii YA, Bodrikov IV, Chiyanov AA, et al. Regiospecific allyl chlorination of betulin and diacetylbetulin. Russ J Org Chem. 2017;53(2):303–304.
   Web of Science ®Google Scholar
• Bodrikov IV, Kurskii YA, Chiyanov AA, et al. Electrophilic substitution of hydrogen in betulin and diacetylbetulin. Russ J Org Chem. 2018;54(1):131–138.
   Web of Science ®Google Scholar
• Bodrikov IV, Borisova NV, Chiyanov AA, et al. Vinylic substitution in the reaction of betulin diacetate with tert-butyl hypochlorite. Russ J Org Chem. 2013;49(1):78–82.
   Web of Science ®Google Scholar
• Miura N, Matsumoto Y, Miyairi S, et al. Protective effects of triterpene compounds against the cytotoxicity of cadmium in HepG2 cells. Molec Pharm. 1999;56:1324–1328.
   PubMed Web of Science ®Google Scholar
• Akihisa T, Takamine Y, Yoshizumi K, et al. Microbial transformations of two lupane-type triterpenes and anti-tumor-promoting effects of the transformation products. J Nat Prod. 2002;65:278–282.
   PubMed Web of Science ®Google Scholar
• Gutierrez-Nicolas F, Gordillo-Roman B, Oberti JC, et al. Synthesis and anti-HIV activity of lupane and olean-18-ene derivatives. Absolute configuration of 19,20-epoxylupanes by VCD. J Nat Prod. 2012;75:669–676.
   PubMed Web of Science ®Google Scholar
• Bębenek E, Kadela-Tomanek M, Chrobak E, et al. New acetylenic derivatives of betulin and betulone, synthesis and cytotoxic activity. Med Chem Res. 2017;26:1–8.
   PubMed Web of Science ®Google Scholar
• Gorbunova MN, Krainova GF, Kisel’kov DM, et al. Copolymers of betulin esters and silver nanocomposites based on them. Rus. J. Appl. Chem. 2016;89:439–446.
   Web of Science ®Google Scholar
• Ortiz A, Soumeillant M, Savage SA, et al. Synthesis of HIV-Maturation Inhibitor BMS-955176 from betulin by an enabling oxidation strategy. J Org Chem. 2017;82:4958–4963.
   PubMed Web of Science ®Google Scholar
• Pettit GR, Melody N, Chapuis JC. Antineoplastic agents. 606. The betulastatins. J. Natural Prod. 2018;81:458–464.
   PubMed Web of Science ®Google Scholar
• Lamoureux M, Milne J. Selenium chloride and bromide equilibria in aprotic solvents; a 77Se NMR study. Polyhedron. 1990;9:589–595.
   Web of Science ®Google Scholar
• Maaninen A, Chivers T, Parvez M, et al. Syntheses of THF solutions of SeX2 (X – Cl, Br) and a new route to selenium sulfides SenS8-n (n – 1-5): X-ray crystal structures of SeCl2(tht)2 and SeCl2·tmtu. Inorg Chem. 1999;38:4093–4097.
   Web of Science ®Google Scholar
• Garratt DG, Schmid GH. The isolation of an episelenurane from the reaction of 4-tolueneselenenyl chloride with ethylene. Can J Chem. 1974;52:1027–1028.
   Web of Science ®Google Scholar
• Smit WA, Zefirov NS, Bodrikov IV, et al. Episulfonium Ions: Myth and Reality. Acc Chem Res. 1979;12(6):282–288.
   Google Scholar
• Smit WA, Zefirov NS, Bodrikov IV. Chemistry of episulfonium ions and mechanism of AdE-reactions of alkenes with sulfenil derivatives. In: RK Freidlina, editor. IUPAC organic sulfur chemistry. Oxford: Pergamon Press; 1981. p. 159–173.
   Google Scholar
• Olah GA, Schilling P, Westerman PW, et al. Electrophilic reactions at multiple bonds. II. Observation and differentiation of intermediate σ and π complexes in electrophilic additions to Ethene, 2,3-Dimethyl-2-butene, and Adamantylideneadamantane. J Am Chem Soc. 1974;96(11):3581–3589.
   Web of Science ®Google Scholar
• Gaussian 09, Revision A.1, Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian, Inc., Wallingford CT.–2009.
   Google Scholar