Chapter 12, Problem LGP

The problem below is directed toward devising a hypothetical pathway for the synthesis of the acyclic central portion of Crixivan (Merck and Company’s HIV protease inhibitor). Note that your synthesis might not adequately control the stereochemistry during each step, but for this particular exercise chat is not expected.

Fill in missing compounds and reagents in the following outline of a hypothetical synthesis of the acyclic central portion of Crixivan. Note that more than one intermediate compound may be involved between some of the structures shown below.