Scorzocreticin (S)-1 was isolated from a plant that is used for cooking traditional meat dishes on the Greek island of Crete. As part of a recent synthesis of scorzocreticin (S)-1, compound 1 was converted into compound 2. (Tetrahedron 2014, 43, 8161-8167.) Identify a synthetic route for converting 1 into 2, knowing that it involves a Wittig reaction. RO. OR a) H+, 1 OH i RO. b) H₂, Pt c) H₂, Lindlar's catalyst d) conc. H₂SO4, heat HO OR 2 OH The transformation above can be performed with some reagent or 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. OH e) RCO3H OMe Scorzocreticin (S)-1 i) PCC, CH₂Cl2 f) 1) MeMgBr; 2) H3O+ g) Ph3P=CH2 h) Na₂Cr₂O7, H₂SO4, H₂O 1) H3O+ j) BH3-THF, H₂O2, NaOH k) 1) LiAlH4; 2) H3O+

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Propose a synthesis for the given reaction.

Scorzocreticin (S)-1 was isolated from a plant that is used for cooking traditional meat dishes on the Greek island of Crete. As part of a
recent synthesis of scorzocreticin (S)-1, compound 1 was converted into compound 2. (Tetrahedron 2014, 43, 8161-8167.) Identify a
synthetic route for converting 1 into 2, knowing that it involves a Wittig reaction.
RO
OR
a) H+,
OH
요
RO.
b) H₂, Pt
c) H₂, Lindlar's catalyst
d) conc. H₂SO4, heat
НО.
OR
2
OH O
The transformation above can be performed with some reagent or 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.
OH
e) RCO3H
OMe
Scorzocreticin (S)-1
i) PCC, CH₂Cl₂
j) BH3.THF, H₂O2, NaOH
k) 1) LiAlH4; 2) H3O+
f) 1) MeMgBr; 2) H3O+
g) Ph3P=CH2
h) Na₂Cr₂O7, H₂SO4, H₂O I) H3O+
Transcribed Image Text:Scorzocreticin (S)-1 was isolated from a plant that is used for cooking traditional meat dishes on the Greek island of Crete. As part of a recent synthesis of scorzocreticin (S)-1, compound 1 was converted into compound 2. (Tetrahedron 2014, 43, 8161-8167.) Identify a synthetic route for converting 1 into 2, knowing that it involves a Wittig reaction. RO OR a) H+, OH 요 RO. b) H₂, Pt c) H₂, Lindlar's catalyst d) conc. H₂SO4, heat НО. OR 2 OH O The transformation above can be performed with some reagent or 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. OH e) RCO3H OMe Scorzocreticin (S)-1 i) PCC, CH₂Cl₂ j) BH3.THF, H₂O2, NaOH k) 1) LiAlH4; 2) H3O+ f) 1) MeMgBr; 2) H3O+ g) Ph3P=CH2 h) Na₂Cr₂O7, H₂SO4, H₂O I) H3O+
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