[Singingintain]

I need to come up with synthesis for the two reactions.

I thought of using Diels Alder for the first one, but you would have to break aromaticity. The methoxy group is ortho/para activating, so i could add a strong electron donating group to the para position, which would then activate it's para position or the methoxy's meta. However, I'm not sure how to cyclized the side group or if this method even work.

Thanks for your *delete me*

[AWK]

1. What about Friedel-Crafts followed by cyclization?
2. What about a Grignard reaction with an aldehyde?