Question

1) Choose one molecule from the set and create an 8-step synthesis scheme using the chosen molecule as your starting material. You need to write the complete set of reagents and draw the product expected from each step. Reagents typically used together are considered one step, e.g. 1) LAH 2) H2O should be considered as one step. Your 8 steps must include at least one reaction from each of the chapters, aldehydes and ketones, carboxylic acid derivatives, alcohols. You can repeat a reaction only once therefore your scheme could have 2 oxidations maximum etc. More specifically, your scheme can include: a) oxidations b) reductions c) Grignard reactions d) acetal formation/cleavage e) Wittig reactions f) reactions or synthesis of an acid chloride, ester, amide or anhydride g) a reaction with SOCl2 or PB h) any reaction to synthesize or react alcohols 1) Imine/enamine synthesis/hydrolysis 1) novel reagents such as Gilman and modified reducing agents. 8-stop Synthetic Scheme:

Answer 1

0 LAH4, THF, it shootou OH 5h Y OH DMP, DCM rt, BH Mg, THF H+, HO o TBS, DMF MeMgBr 4 equiv. 0°C OTBS OTBS, OTBS 1.OH THF, reflux, h 03. DCM -78 C, 30 min PPH3, it, 6 h HF, THE РСС, D CM о он or modo он I ... LOH DCMM gSO4

eight step