Talk:Merrilactone A

Total synthesis scheme

In total synthesis scheme image, compounds 15 and 16 are identical. —Preceding unsigned comment added by 77.38.183.85 (talk) 20:16, 14 December 2009 (UTC)

That's not the only issue with the synthetic scheme.

1. The reaction conditions for the transformation from 16 to 17 should be TIPSOTf and Et₃N not TIPSOf and Et₃
2. 25 should have an OCO₂Et group, not a CO2Et group.
3. In reference to the above issue, both 16 and 17 should have a Br in place of the SnBu₃ group. 17 should be a furan, with TIPS-protection occuring alonside elimination.
4. Compound 14 should have an alcohol instead of the ketone.
5. Finally, the Weinreb Amide is not reacted with aldehyde 18, but rather with the lithiate generated by lithium-halogen exchange directly on the correct structure for 17, which again is a furan with a bromide instead of a stannane. 18 was in fact an intermediate synthesized on an earlier attempted path which failed.

File:Total synthesis.png

Furthermore, the catalyst should have 2 equivalents of the monoanionic B(Ar_f)counterion rather than 1 equivalent of the dianionic compound (which doesn't even make sense for boron). I would also suggest inclusion of the catalyst into the main synthetic scheme instead of leaving it separate.

File:Ir(III) catalyst.png

M.Levin 20:03, 5 January 2011 (UTC)

I have tagged it on commons. --Makecat_Talk 03:37, 27 September 2012 (UTC)

For now, I have removed the entire section because of the multiple errors. When someone fixes the images, it can be reintroduced. ChemNerd (talk) 21:58, 9 November 2012 (UTC)

• I would think that if content is disputed a dispute tag is put up first. If you really have to you can remove the disputed content after some time. Now you have also removed undisputed content. Please restore undisputed sections. V8rik (talk) 12:57, 10 November 2012 (UTC)

This discussion has been here since 2009, so clearly the waiting of "some time" has already occurred. Leaving incorrect content in the article for nearly three years while waiting for someone to fix it seems more than long enough to me. The content I removed was the disputed diagram plus all the text that refers directly to items in the diagram (and therefore, of course, are not useful without the diagram). I suppose the first sentence from the removed section could be restored as undisputed, so I don't mind if you would like to do so. ChemNerd (talk) 13:40, 12 November 2012 (UTC)

• We are in agreement V8rik (talk) 18:28, 13 November 2012 (UTC)