Compound 3 below, called mycoepoxydiene, has been isolated from a marine fungus and has been shown to possess anti-cancer and anti-inflammatory properties. It contains an unusual oxygen-bridged cyclooctadiene skeleton. Both enantiomers of this compound were made in the laboratory. (Org. Lett. 2002, 4, 2941-2943). Show the reagents you would use to convert compound 1 into compound 2. H3COCO,,, 1 OTBDMS CH3 2 A. conc. H₂SO4, heat D. 1) BH3-THF; 2) H₂O2, NaOH OTBDMS B. Br2 E. HBr CH3 C. H₂, Pt Many steps F. t-BuOK O 3 "O The transformation above can be performed with some combination of the reagents listed below. Give the necessary reagents in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. ""H CH3 CH3 TDBMS = -Si-t-Bu CH₂

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Chapter1: Chemical Foundations
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Compound 3 below, called mycoepoxydiene, has been isolated from a marine fungus and has been shown to possess anti-cancer and
anti-inflammatory properties. It contains an unusual oxygen-bridged cyclooctadiene skeleton. Both enantiomers of this compound
were made in the laboratory. (Org. Lett. 2002, 4, 2941-2943). Show the reagents you would use to convert compound 1 into compound
2.
(C
CH3
1
OTBDMS
2
A. conc. H₂SO4, heat
D. 1) BH3-THF; 2) H₂O2, NaOH
B. Br2
OTBDMS
E. HBr
CH3
C. H₂, Pt
Many
steps
F. t-BuOK
H3COCO,,,
The transformation above can be performed with some combination of the reagents listed below. Give the necessary reagents in the
correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide
just one answer.
3
'H
CH3
CH3
TDBMS = -Si-t-Bu
CH3
Transcribed Image Text:Compound 3 below, called mycoepoxydiene, has been isolated from a marine fungus and has been shown to possess anti-cancer and anti-inflammatory properties. It contains an unusual oxygen-bridged cyclooctadiene skeleton. Both enantiomers of this compound were made in the laboratory. (Org. Lett. 2002, 4, 2941-2943). Show the reagents you would use to convert compound 1 into compound 2. (C CH3 1 OTBDMS 2 A. conc. H₂SO4, heat D. 1) BH3-THF; 2) H₂O2, NaOH B. Br2 OTBDMS E. HBr CH3 C. H₂, Pt Many steps F. t-BuOK H3COCO,,, The transformation above can be performed with some combination of the reagents listed below. Give the necessary reagents in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. 3 'H CH3 CH3 TDBMS = -Si-t-Bu CH3
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