16.48 D is an intermediate in the synthesis of rosiglitazone (trade name Avandia), a drug used to treat type 2 diabetes. Suggest two different methods to prepare the ether in D by substitution reactions. CHO D rosiglitazone H
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- 17.36 Tamoxifen is an estrogen receptor modulator that is used in the treatment of breast cancer. Provide the missing reagents and the structure of compound A in the synthesis of tamoxifen. Page 707 HO (CH3)2N 1. C,H,MgBr 2. H + Compound A (CH3)2N TamoxifenQuinapril (trade name Accupril) is used to treat high blood pressure andcongestive heart failure. One step in the synthesis of quinapril involvesreaction of the racemic alkyl bromide A with a single enantiomer of theamino ester B. Given the structure of quinapril, which one of these two products isneeded to synthesize the drug?Enalapril, a drug used to treat hypertension, is prepared from compounds D and E by reductive amination. What is the structure of enalapril?
- MeO 22.55 One potential synthesis of the anti-inflammatory and analgesic drug nabumetone is chloromethylation (Problem 22.48) of 2-methoxynaphthalene followed by an acetoacetic ester synthesis (Section 19.6). 5 3 6 CH₂O CI acetoacetic ester synthesis HC 7 MeO MeO 1 8 2-Methoxynaphthalene Nabumetone (a) Account for the regioselectivity of chloromethylation at carbon 6 rather than at carbon 5 or 7. (b) Show steps in the acetoacetic ester synthesis by which the synthesis of nabum- etone is completed.18.18 Provide a structural formula for the product from each of the following reactions. (a) (c) (e (1) LDA (2) CH,CH,I NaH CI (b) (d) O. (f Br, CH,CO,H Br, (excess), NaOHD is an intermediate in the synthesis of rosiglitazone (trade name Avandia), a drug used to treat type 2 diabetes. Suggest two different methods to prepare the ether in D by substitution reactions.
- 18.31 Aldehydes that have no a hydrogen undergo an intermolecular oxidation-reduction called the Cannizzaro reaction when they are treated with concentrated base. An example is the following reaction of benzaldehyde: ororo H HO™ OH H₂O 2 + (a) When the reaction is carried out in D₂O, the benzyl alcohol that is isolated contains no deuterium bound to carbon. It is CBH-CH₂OD. What does this suggest about the mechanism for the reaction? (b) When (CH3)2CHCHO and Ba(OH)₂/H₂O are heated in a sealed tube, the reaction produces only (CH3)₂CHCH₂OH and [(CH3)₂CHCO₂]2Ba. Provide an explanation for the formation of these products.18.20 Write a stepwise mechanism for each of the following reactions. (a) O H (c) O HOG NaOH, H₂O -A NaOH, H₂O d of Plz solve all parts within 30-40 I'll upvote your answer (b) CH3 H NaOD D₂O you bou H D CH3 O Then shAttenol A and pinnatoxin A are natural products isolated from marine sources. (a) Locate the acetals, hemiacetals, imines, and enamines in both compounds. (b) Draw the hydrolysis product formed when attenol A is treated with aqueous acid. Include stereochemistry at all stereogenic centers.
- Predict the products of reactions of ethers and epoxides, including the following:(a) Cleavage and autoxidation of ethers(b) Acid- and base-promoted opening of epoxides(c) Reactions of epoxides with organometallic reagents(d) Cleavage of silyl ethersRank the compounds in each of the following groups in order of their reactivity to electrophilic substitution: (a) Nitrobenzene, phenol, toluene, benzene (b) Phenol, benzene, chlorobenzene, benzoic acid (c) Benzene, bromobenzene, benzaldehyde, anilineRank the following compounds in order of increasing acidity and explain in detail your choice of order.