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 380xx-360 MeO G. HBr D. DMP or PCC H MeO B. H₂SO4, H₂O, HgSO4 E. Na₂Cr₂O7, H₂SO4, H₂O H. 1) O3; 2) DMS H H 2 Meo 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 Me H Galanthamine OH

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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
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
OH
Transcribed Image Text: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 OH
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