Atorvastatin (Lipitor) is used to decrease patient serum cholesterol levels. It worksby inhibiting an enzyme called HMG-COA reductase. See"Connections to BiologicalChemistry"one synthesis of atorvastatin that produces the desired single enantiomer of the finalproduct, the following reagents are used. Draw the structures of synthetic intermedi-ates A and B.In-ClNaCNНО.ABDMSOPyridine

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Answered: Atorvastatin (Lipitor) is used to…

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter10: Alcohols

Section: Chapter Questions

Problem 10.57P

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A chiral amine A having the R conguration undergoes Hofmann elimination to form an alkene B as the major product. B is oxidatively cleaved with ozone, followed by CH3SCH3, to form CH2 = O and CH3CH2CH2CHO. What are the structures of A and B?
Permethrin and Bifenthrin Pyrethrin is a natural insecticide obtained from the powdered flower heads of several species of Chrysanthemum. The active substances in pyrethrum, principally pyrethrins I and II, are contact poisons for insects and cold-blooded vertebrates. Although powders made from Chrysanthemum extracts have found widespread use, the active substances in them are destroyed rapidly in the environment. In an effort to develop synthetic compounds as effective as the natural insecticides but with greater biostability, chemists prepared a series of esters related in structure. Among the synthetic pyrethrenoids now in common use in household and agricultural products are permethrin and bifenthrin. As discussed above, the natural products pyrethrins I and II (not shown) are destroyed rapidly in the environment. One of the key changes in the structures of permethrin and bifenthrin relative to the pyrethrins was the substitution of naturally occurring methyl groups on the alkene with electron withdrawing groups (EWGs) such as chlorine and trifluoromethyl. What reactions of the alkene would the change of methyl groups to EWGs retard? 1. Oxidation of the double bond. 2. Electrophilic addition reactions. 3. Nucleophilic addition reactions. 4. Both 1 and 2. 5. All of the above.
Predict the neutral products of the reaction. Clearly show stereochemistry by drawing a wedged bond, a dashed bond and two in‑plane bonds for the chiral carbon.
Write structures for products A, B, C, and D showinf stereochemistry. (Hint: B and D are stereoisomers)
Quinapril (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?
Compound W shows stereoisomerism. Why are such isomers formed in approximately equimolar quantities no matter the synthetic pathway used for the preparation of the compound?
The chiral hydroxyl compound P, C7H14O contains a five-membered ring and showspositive result in iodoform test. Compound P and sodium bromide can be produced byrefluxing compound Q with aqueous NaOH solution. Compound P is heated withbenzoic acid in the presence of concentrated H2SO4 to form a sweet-smelling product,compound R. Deduce the structure of P, Q and R. PLEASE PROVIDE CLEAR HAND WRITING AND SOLUTIONS
Hydrogenation of alkene A with D2 in the presence of Pd-C affords a single product B. Keeping this result in mind, what compound is formed whenA is treated with each reagent: (a) mCPBA; (b) Br2, H2O followed by base? Explain these results.
Organotin compounds play a significant role in diverse industrial applications. They have been used as plastic stabilizers and as pesticides or fungicides. One method used to prepare simple tetraalkylstannanes is the controlled direct reaction of liquid tin(IV) chloride with highly reactive trialkylaluminum compounds, such as liquid triethylaluminum (Al(CzHs)3). 3SnCl4 + 4Al(C2H5)3 → 3Sn(C2H5)4 + 4AlCl3 In one experiment, 0.160 L of SnCl4 (d= 2.226 g/mL) was treated with 0.346 L of triethylaluminum (Al(C2H5)3); d = 0.835 g/mL). What is the theoretical yield in this experiment (mass of tetraethylstannane, Sn(C2H5)4)? If 0.257L of tetraethylstannane (d= 1.187 g/mL) were actually isolated in this experiment, what was the percent yield?
Aldohexoses A and B both undergo Ruff degradation to give aldopentose C. On treatment with warm nitric acid, aldopentose C gives an optically active aldaric acid. B alsoreacts with warm nitric acid to give an optically active aldaric acid, but A reacts to givean optically inactive aldaric acid. Aldopentose C is degraded to aldotetrose D, whichgives optically active tartaric acid when it is treated with nitric acid. Aldotetrose D isdegraded to (+)@glyceraldehyde. Deduce the structures of sugars A, B, C, and D, and useFigure 23-3 to determine the correct names of these sugars.
Diisopinocampheylborane (Ipc2BH) is a chiral organoborane, readily employed for the production of many asymmetric products used in total synthesis. It is a crystalline material that can be prepared as a single enantiomer via the hydroboration of two equivalents of α-pinene with borane.Explain why only one enantiomer of Ipc2BH is formed.
Organotin compounds play a significant role in diverse industrial applications. They have been used as plastic stabilizers and as pesticides or fungicides.One method used to prepare simple tetraalkylstannanes is the controlled direct reaction of liquid tin(IV) chloride with highly reactive trialkylaluminum compounds, such as liquid triethylaluminum (Al(C2H5)3). 3SnCl4 + 4Al(C2H5)3 3Sn(C2H5)4 + 4AlCl3 In one experiment, 0.230 L of SnCl4 (d = 2.226 g/mL) was treated with 0.396 L of triethylaluminum (Al(C2H5)3); d = 0.835 g/mL). If 0.335 L of tetraethylstannane (d = 1.187 g/mL) were actually isolated in this experiment, what was the percent yield?

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