Question

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From any source you like, choose a natural product (an organic compound or substance produced by a living organism that is found in nature) with not more than 18 and not less than six carbon atoms.

Draw the structure of your compound including stereochemical information, report a name, the molecular formula and molar mass. (5 pts.)

Cite one publication that describes the synthesis of this molecule, check e. g. Google Scholar. Use the information for proper citations found under the following web address:

http://library.williams.edu/citing/styles/acs.php (5 pts.)

From this publication, select one synthetic step and describe it (narrative and drawing) including the respective mechanism. Be sure to show pertinent information about this particular reaction mechanism (arrows, reagents, conditions, stereochemistry). (10 pts.)

For the starting material used in the step you selected, identify the groups of homotopic protons and from these, the group with the lowest and the group with the highest shift values. Give an estimate for these shift values. Indicate any chiral centers. (10 pts.)

In not more than 50 words, describe a biochemical function of the natural product you selected. Do not select a natural product for which you cannot find this information.

Answer 1

HO HOIl morphine

Me AcOH MeO oH2 Meo NC OH CuCro NH он CN high pressure N2H/KOH 2. a) Mel, NaH b) LAH Me 13)Br2 но b) 2.4-DNPH 2. HCI но 1. H2SO 2. KOH 3. KOtBu/Ph-CO MeO 3. HzlPtO2 "Gates Intermediate 1. Br2, AcOH 2, 2.4-DNPH 3. HCI HO NHAr но codeine NH pyridine/HC HN-2 NO2 NO

Journal of the American Chemical Society 78 (7): 1380–1393.

molecular formula - C17H19NO3

Morphine is used primarily to treat both acute and chronic severe pain. It is also used for pain due to myocardial infarctionand for labor pains