Retrosynthesis II

Yesterday evening we held our second informal retrosynthesis session in St. John's bar. It was quite good, though the molecule I chose was a little hard. It provided some good discussion with each of us coming up with different approaches, so I think it was quite a useful exercise. The sum of our deliberations was to disconnect the 8-membered ring first and then open the aminal-type centres to amines and carbonyls, envisaging reductive amination as a synthesis. I wondered whether you could disconnect them all at one and stew it up to get the cyclisations you wanted, though we seemed to agree that this might just be wishful thinking.

For the isolation, see JNP 2005 258.