[TheHitokiri]

What's the most stable chair structure for the tricyclic organic compound?

I tried splitting it into 3 sections A, B and C but it still got extremely messy and I got stuck at the bridges. Couldn't seem to be able to fit in section B and section C.

[Archer]

This is quite difficult to draw freehand.

Start at Ring B with the nitrogen atom being the bottom of the chair (the foot of the chair as it were). This should give you a good place to start from.

[TheHitokiri]

I still got stucked at the point where the chair goes out of the plane.

[Dan]

I would also start with the B ring. Now try joining on the A ring.

Look at the structures of cis- and trans-decalin for inspiration:



Now try and connect the C ring - you will find that it is only possible to close the C ring for one of the two possible AB conformations.

[TheHitokiri]

Thanks Dan for the inspiration. Finally figured out, definitely doesn't look like the chair structures we usually see.