5124

 

Identify all of the lettered compounds shown in the sequence below for the synthesis of lysergic acid, a potent hallucinogen.  Assume normal workup after each reaction. (JACS 76, 5256 (1954)

 

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5186

 

Complete the equations below by supplying the missing product:

 

(a)

(b)

(c)

(d)

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5248

 

Juvabione is a compound which intervenes in normal metamorphosis of certain insects.  The steps in its synthesis from starting materials A and B are shown below.  Complete the equations describing its synthesis from A and B by supplying the missing lettered structures.

 

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5269

 

The total synthesis of equilenin, a weakly estrogenic sex hormone isolated from mare's urine, is shown below.  Supply the structures of the compounds of the sequence where they are missing.  [Lit.: W. E. Bachmann, W. Cole, and A. L. Wilds, J. Amer. Chem. Soc., (1940) 62, 824-839.]