Steroids are a class of organic compounds containing a specific tetracyclic skeleton (four rings), as seen in the compounds shown below. During efforts to synthesize a steroid that was isolated from the Atlantic starfish, the side chain of compound 1 was converted into the side chain of compound 2, as highlighted below. Propose a synthesis for this transformation. H,C H,C OH HC HC H. OAc = AcO AcO 2

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Chapter1: Chemical Foundations
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Draw product of the second step.
H,C
-OH
CH3
CH,
AcO
H.
OAc
Edit Drawing
Transcribed Image Text:Draw product of the second step. H,C -OH CH3 CH, AcO H. OAc Edit Drawing
Steroids are a class of organic compounds containing a specific tetracyclic skeleton (four rings), as seen in the compounds shown
below. During efforts to synthesize a steroid that was isolated from the Atlantic starfish, the side chain of compound 1 was
converted into the side chain of compound 2, as highlighted below. Propose a synthesis for this transformation.
OH
H.
HC
H.
OAc =
AcO
1
AcO
2
OAc
X Your answer is incorrect.
Identify reagents for the first step of the synthesis.
O Nac = CH
O TSCI, pyridine
O NaOH
O 03, DMS
Transcribed Image Text:Steroids are a class of organic compounds containing a specific tetracyclic skeleton (four rings), as seen in the compounds shown below. During efforts to synthesize a steroid that was isolated from the Atlantic starfish, the side chain of compound 1 was converted into the side chain of compound 2, as highlighted below. Propose a synthesis for this transformation. OH H. HC H. OAc = AcO 1 AcO 2 OAc X Your answer is incorrect. Identify reagents for the first step of the synthesis. O Nac = CH O TSCI, pyridine O NaOH O 03, DMS
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