[Rutherford]

How to think of a way to synthesize the attached molecule? I have found that it can be easily synthesized with parabenzoquinone and 1,3-cyclohexadiene in a Diels-Alder addition, followed by a photochemically induced [2+2] cycloaddition. Are there any tricks and tips of how to think when doing such problems?

[Rutherford]

For example, how to deduce the starting materials for the following compound:

[clarkstill]

Diels alder between furan and benzyne, then partial ozonolysis to make the secondary ozonide?

[Rutherford]

Could there be a pathway with singlet oxygen?

[clarkstill]

Not that I can see. The only place singlet oxygen could be incorporated is where the peroxy ether is, but I don't see how this could easily arise through cycloaddition chemistry with anything that looks reasonable.

[Rutherford]

How does the ozonide formation work?

[Dan]

How does the ozonide formation work?

Google "ozonolysis mechanism", or look it up in any organic chemistry textbook. It's a classic.

[clarkstill]

See attached.

[Rutherford]

Now I understand. Thank you very much.