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- Identify A through O:The key step in a reported laboratory synthesis of sativene, a hydrocarbon isolated from the mold Helminthosporium sativum, involves the following base treatment of a keto tosylate. What kind of reaction is occurring? How would you complete the synthesis?The double bond of an enamine (alkene + amine) is much more nucleophilic than a typical alkene double bond. Assuming that the nitrogen atom in an enamine is sp2hybridized, draw an orbital picture of an enamine, and explain why the double bond is electron-rich.
- 19.69 Propose an efficient synthesis for each of the following transformations: (a) (b) (c) Br Br -C MeO OMeParoxetine (Paxil) is an antidepressant that is a member of a family of drugs known as Selective Serotonin Reuptake Inhibitors (SSRIS). This family of drugs also includes fluoxetine (Prozac) and sertraline (Zoloft). SSRIS work by inhibiting the reuptake of the neurotransmitter serotonin in the synapses of the central nervous system follow- ing release of serotonin during excitation of individual nerve cells. Between firings, the serotonin is taken back up by a nerve cell in preparation for firing again. Inhibition of reuptake has the effect of increasing the time serotonin molecules remain in the syn- apses following excitation, leading to a therapeutic effect. In one synthesis of parox- etine, the following reagents are used. Draw the structures of synthetic intermediates A and B. F НО SOCI, A B HO Pyridine18.65 Propose a plausible synthesis for the following trans- formation. CH3 CH3 CH3
- 19.70 Draw a plausible mechanism for the following transformation: NH2 [H2SO4] NH2 (-H₂O)15.41 Draw the structures of the aldehydes that might be oxi- dized to yield the following carboxylic acids: (a) COOH (b) CH2COOH ČH3 OH (c) CH,CH=CHCH,COOH17.36 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 Tamoxifen
