As we will see in Chapter 26, 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 (Tetrahedron 2003, 59,8623-8628), the side chain of compound 1 was converted into the side chain of compound 2, as highlighte below. Propose a synthesis for this transformation. Aco H₂C O NaOH O 1) O3; 2) DMS O NaC=CH O TSCI, pyridine H₂C H OAC H OH Aco H₂C A H H₂C H ŌAc H This transformation can be accomplished in three steps. Identify the reagent(s) for the first step of the synthesis. O (ox - Hol) OAc=

As we will see in Chapter 26, 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 (Tetrahedron 2003, 59,8623-8628), the side chain of compound 1 was converted into the side chain of compound 2, as highlighte below. Propose a synthesis for this transformation. Aco H₂C O NaOH O 1) O3; 2) DMS O NaC=CH O TSCI, pyridine H₂C H OAC H OH Aco H₂C A H H₂C H ŌAc H This transformation can be accomplished in three steps. Identify the reagent(s) for the first step of the synthesis. O (ox - Hol) OAc=

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Concept explainers

Reactions of Ethers

Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.

Epoxides

Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.

Williamson Ether Synthesis

An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.

Question

As we will see in Chapter 26, 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
(Tetrahedron 2003, 59, 8623-8628), the side chain of compound 1 was converted into the side chain of compound 2, as highlighted
below. Propose a synthesis for this transformation.
Aco
H₂C
O NaOH
O 1) 03; 2) DMS
O NaC=CH
O TSCI, pyridine
H₂C
OAc
OH
Aco
H₂C
H
H₂C
H
ŌAC
2
O
OAc =
This transformation can be accomplished in three steps. Identify the reagent(s) for the first step of the synthesis.

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