a)i) Apply Lipinski’s Rules to the structure of indinavir.

a)ii) What does your Lipinski analysis tell you about the suitability of indinavir as a drug? Briefly explain the limitations of this analysis.

b)i) Demonstrate your understanding of retrosynthetic analysis by redrawing step (iii) in the retrosynthetic direction. Show the disconnection, retrosynthetic arrow, and synthons corresponding to the starting materials.

b)ii) Two separate reactions are achieved in step (iv). Briefly explain what each of these is and use your answer to illustrate why the tert-butyloxycarbonyl (Boc) protecting group used for protection of 5 was a better choice than use of a fluorenylmethylcarbonyl group (Fmoc).

N. OH OH Indinavir 1 Molecular Weight: 613.80 logP: 2.49 ZI