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- 5. Assign R or S configuration to each chirality center in the following molecules: CH3 CH3 Br (a) Br (b) (c) HaCH3 HaBr H OH CH3 H3C H OH H CH3 OH Which of these compounds are enantiomers, and which are diastereomers?Simvastatin (trade name: Zocor™M) is a pharmaceutical used to treat elevated blood lipids (i.e. high cholesterol). It contains 7 chirality centers (which allows for 128 different stereoisomers!) Determine the configuration of each chirality center. HOL. O CH3 H O H Ou yot H O XII H по / CH3Coibacin B (shown below) is a natural product that exhibits potent anti-inflammatory activity and potential activity in the treatment of leishmaniasis, a disease caused by certain parasites (Org. Lett. 2012, 14, 3878-3881): (a) Assign the configuration (R or S) of each chirality center (labeled A to C) in coibacin B. (b) Identify the number of possible stereoisomers for this compound, assuming that the geometry of the alkenes are fixed. Choices are given below and write the CAPITAL LETTER of your choice. A. 2 В. 4 С. 8 D. 16 ANSWERS: (a) A. В. C. (b)
- Simvastatin (trade name: ZocorTM) is a pharmaceutical used to treat elevated blood lipids (i.e. high cholesterol). It contains 7 chirality centers (which allows for 128 different stereoisomers!) Determine the configuration of each chirality center. H H HO H H H H H H H H H O H H4. Consider the structure of Rifamvcin B shown below. Assign configuration around marked with circle chirality centers. Но, ОН OH OH NHAns: 2. Assign the absolute configuration of the chirality center as R or S. O HO- Ans: Assign the absolute configuration of the chirality center as R or S. Ans: OH 3. Drawn below is the structure of Crestor® (rosuvastatin), a medication used to reduce cholesterol. Assign the absolute configurations of the two chirality centers as R or S. | NH 4. What is the relationship of the following two structures? OH OHI NH OH OH A. Enantiomers B. Diastereomers. C. Constitutional isomers D. Identical Ans: NH CO₂H 5. What is the relationship of the following two structures? OH OH A. Enantiomers B. Diastereomers C. Constitutional isomers D. Identical Ans: Loo HO OH 6. What is the relationship of the following two structures? HO HO \,.. ...NH محمد HO OH eilte neu-1071 Mamos a diartwollen preto a
- VIII. Assign R, S configurations to each chirality center in the molecule below. Br CH3 X OH CH3 I I (1. Consider the following pairs of structures. Designate each chirality center as (R) or (5) and identify the relationship between them by describing them as representing enantiomers, diastereomers, constitutional isomers, or two molecules of the same compound. Use handheld molecular models to check your answers. HG (a) Br and and CH H,G H (b) and CH, Br Br 'F (k) and Br CI Br (e) and CH, CH, CH CH, CH, H- -H- CH and H- -Br (d) and FCH CH, CH, Br H CH, and (m) (e) and H. Br CH, and (m) and Br CH (o) and nd and and andWhich of the following statements is/are true of compound C given below? OH HO Compound C OH (i) The boiling point of compound C is higher than the boiling point of (ii) The chirality centre (stereocentre) of compound C is of S configuration. CI (iii) Compound C reacts with SOCI, in pyridine to form CI O Only statements (ii) and (iii) are true. O All three statements are true. O Only statement (i) is true. O Only statement (ii) is true. O Only statement (iii) is true.
- 8. Two structures of Lipitor (a drug used to lower cholesterol) are shown below. (a) Determine the absolute configuration of each indicated stereocenter. Fill in the correct circle. (b) Determine if the two structures are the same compound or stereoisomers. Fill in the correct circle. (a) НО. Carbon a HO O OH Carbon a: OR OS Carbon b H N Carbon b: R OS of H Carbon c: OR OS OH OH Carbon c F Carbon d: R OS OH Carbon d (b) The two structures are: O the same compound O stereoisomers11. Consider the following compounds: ÇO,H CHO ОНС H. ОНС CO,H H3C- -- H. HO- H3C H. O, H ČOH HO, CH3 B (a) Label the asymmetric carbons as R or S on each compound (A - C). (b) Which compounds, if any, are enantiomers? diastereomers? identical?Identify (circle) all the chirality centers НО
