[luenne]

I want to do the Retrosynthesis plan for the following 2 compounds. The left part of the two compounds is relatively similar so I thought I would start on that. I am using Reaxys. But so far no luck. Does anyone know which part would be an obvious choice to start on?

[discodermolide]

Break the bond between the left part nitrogen and the carbon, gives you a left part NH which can be alkylated with an alkyl halide right hand part or reactively aminated with a right hand aldehyde.Try that and see where it gets you.

[luenne]

Thanks a lot for the fast reply. I found out that the compound on the left is commercially available (reaxys), please find it attached. But how do I mount the Florine and the 2 Nitrogens on form part of Compound 1, and respectively the 2 nitrogens on compound 2. any ideas?

[discodermolide]

You can't use the 2,3,4,9-tetrahydro-1H-fluorene as a starting material. There is no way to get the N atoms in that ring system. I won't even mention the F atom.

[luenne]

I know some steps are probably not feasible, but would that be (theoretically) correct?

[fledarmus]

I think you'll find it more feasible to do your second disconnection on the pyridine ring rather than a pendant alkane on a cyclohexyl ring.