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- Galantamine, a natural product produced by the amaryllis family of flowering plants, has been used in the early treatment of Alzheimer's disease. In a synthesis of galantamine and related compounds (J. Org. Chem. 2015, 80, 1952-1956), compound 1 was converted into compound 2. Propose an efficient synthesis for the conversion of 1 to 2 A. NaOH MeO D. DMP or PCC G. HBr MeO B. H₂SO4, H₂O, HgSO4 E. Na2Cr₂O7, H₂SO4, H₂O H. 1) O3; 2) DMS H 2 The conversion of 1 to 2 can be performed with some reagent or combination of the reagents listed below. Give the necessary reagents in the correct order for each transformation, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. C. 1) BH3-THF; 2) H₂O2, NaOH F.HBr, ROOR I. TsCl, py Meo I₁, N Me Galanthamine OHThis synthesis scheme was designed using the reaction roadmaps. (Reaction roadmaps allow you to "navigate" between the different functional groups and their behavior in chemical reactions.) compound c compound b ● W compound a compound f MAVI compound e m compound d Reagents HBr HBr, H₂O₂, hv a. b. c. H₂O, H₂SO4 d. Br₂ e. Cl₂ f. H₂, Pd Br₂, H₂O Cl₂, H₂O OsO4 then NaHSO3 #[ ] در g. h. i. j. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • If there are alternative structures, draw the most stable one. • If the reaction produces a racemic mixture, draw both stereoisomers. Separate structures with + signs from the drop-down menu. k. I. m. n. O. p. Hg(OAc)2, H₂O then NaBH4 BH3 then H₂O₂, NaOH O3 then (CH3)2S In this synthesis, reagents from the table are used to carry out the indicated steps (shown in blue). In the box below, draw the structure of compound d. q. r. 2 equivalents of NaNH₂ H2, Lindlar's catalyst Na/NH3 H₂SO4, HgSO4 (sia)2BH then H₂O₂, NaOH 1…The second part of the synthesis of 1 involves conversion from compound 5 to compound 8. N. TMSCN condition B reagent C Но- -N. N. BnO > 7 - H* H* "CN ОН Bno OBn 5 8 3a. TMSCN has the structure of (CH3)3 Si-CN and can be considered as an equivalent of cyanide ion, CN-. Deduce the structure of compound 6. 3b. Compound 6 is then converted to compound 8, via compound 7. Draw the structure of 7, condition B and reagent C.
- Galantamine, a natural product produced by the amaryllis family of flowering plants, has been used in the early treatment of Alzheimer's disease. In a synthesis of galantamine and related compounds (J. Org. Chem. 2015, 80, 1952-1956), compound 1 was converted into compound 2. Propose an efficient synthesis for the conversion of 1 to 2 A. NaOH MeO D. DMP or PCC G. HBr 1 MeO B. H₂SO4, H₂O, HgSO4 E. Na₂Cr₂O7, H₂SO4, H₂O H. 1) O3; 2) DMS H 2 x I. TsCl, py The conversion of 1 to 2 can be performed with some reagent or combination of the reagents listed below. Give the necessary reagents in the correct order for each transformation, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. C. 1) BH3-THF; 2) H₂O2, NaOH F.HBr, ROOR = MeO Ill. N Me Galanthamine OHA. OH Provide an effective synthesis of the product below. Show all steps and structures of compounds, and write all of the necessary reagents for this synthesis.3. Propose a synthesis from benzene and show each intermediate Br NH₂
- Propose an efficient synthesis for the following transformation. Use the reagents/conditions below and enter your answer as a string of letters with no spaces or punctuation. но A. H3O* B. conc. H2SO4 C. NaOEt D. t-BUOK Е. HBr F. HBr, ROOR G. TSCI, pyridine H. BH3-THF then H202, NaOH I. Hg(OAc)2, H2O, then NaBH4 J. Br2, UV light K. OsO4, NMO L. MCPBAPropose an efficient synthesis for the reaction below using any necessary organic and inorganic reagents. HO ОН ? Hill... H3C 1111CH3 H15) Propose a synthetic route to convert 3-methyl-1-butanol into 3-methyl-2-butanol. OH OH A) 1. NaOH; 2. H3O+ B) 1. H₂SO4, heat; 2. NaBH4; 3. H3O+ C) 1. H2SO4, heat; 2. Hg(OAc)2, H2O; 3. NaBH4 D) 1. Hg(OAc)2, H2O; 2. H2SO4, heat; 3. NaBH4 E) 1. NaOMe; 2. BH3-THF; 3. H2O2, NaOH Answer: C
- Provide the reagents necessary to carry out the following conversion using a Stork enamine synthesis. O LO -O; H3O+ CH3NH/H₂SO4; NaOCH 3; (CH3)2NH/H2SO4; (CH3)2NH/H2SO4; CH3NH/H₂SO4; =O; H3O+ =O; H3O+ -O; H3O+ FO; H3O+Choose the reagents that can be used to perform the following transformation: Select one: a. "OH, H₂O ...OH e. OH b. H3O+ X c. Na₂Cr₂O7, H₂SO4 d. KMnO4, OH Both -OH, H₂O and H3O+ (separately) will work.Show reasonable mechanisms for the following reaction.