CHEM 0350 TA Problems Week 9 Solutions

Problem 1 Box problems! CHEM 0350 TA Problems Monday - Week 9 Compound A below has been used in a variety of synthetic pathways, but you are given a limited amount of information to figure out its structure. Fill in the empty boxes below with structures of compounds as appropriate. Indicate all relative stereochemistry. In addition, please also specify the number of isomers formed in each reaction and their relationship (diastereomers, enantiomers, etc.). 2 diastereomers Ph OH Ph OH Ph OH Ph OH 2 diastereomers H2SO4 H 2O (5%) 1) Hg2+ , H 2O A 2) NaBH 4 1) R 2 BH 2) H2O2 , NaOH 1) O3 2) Me2S Ph Ph OH OH 2 diastereomers O 1Ph O product Ph Ph Ph H 2 / Pd A Ph 1) OsO4 OH OH 2) NaHSO3, H 2O OH OH 2 diastereomers These problems are tricky! Take your time and make sure you understand the mechanism by which each of the above steps occurs; this will be invaluable on exam day. If you have any questions about any of these box problems, feel free to talk to me during problem session; I’d love to go over them with you in more detail!