[Kamickalo]

In the above image, what does it mean to have the 'R' group cross the phenyl ring like that? It doesn't appear to be bound to any particular carbon - the bond is just crossing over one of the other bonds. What is this supposed to mean?

As a bonus, does anyone know how I can draw it in MarvinSketch or SymyxDraw?

[Messi]

I think it means it is bonded to one of the carbons in the ring, but the authors did not bother to  mention where.

[curiouscat]

I think it means it is bonded to one of the carbons in the ring, but the authors did not bother to  mention where.

Not "did not bother".

It's more like "doesn't matter where" or "any position will be OK"

It is intentionally ambiguous not carelessly vague.

[Messi]

Does not matter where therefore did not bother

[curiouscat]

Does not matter where therefore did not bother

Gotcha! 

I was being pedantic. 

[orgopete]

Since the title of the scheme includes "and analogs", the R-group refers to the analogs being prepared. I presume there are a number of different analogs that were prepared, but not all in the same position. They were using a more generic description in which the R-group is more specifically defined elsewhere. The scheme shows R does not equal hydrogen, but it does not specify what it is. They could have made a 4, 5, 6, or 7-methyl analog and used this form of R rather than an R_i format specifying each group. It was just a shorthand notation.