144 Hr Transit

No, unfortunately, this is not possible and your concern about the two regions is correct. You cannot have two Chinese regions in the row within one 144 hours visa free transit. Maybe you could think about doing the following:

US - Hong Kong - Guangzhou - Macau

Like this, you would become eligible for 144 hours visa free transit in Guangdong province. After that:

Macau - Shanghai - US

This option would allow you to enjoy 144 hours in the second Chinese transit region without any problem.

You do not have to stay in Macau any single night after you have exited from Guangdong province, but you can just continue to the airport to take a flight to Shanghai.

One more detail...

You need to have in mind that in order to be eligible for 144 hours visa free transit for Guangdong province, you will have to fly from Hong Kong to Guangzhou.

Also, when you land in Guangzhou, you will have to present the ticket of how will you depart to Macau (if you decide for this option) and in this case, I suggest you to book TurboJet ferry ticket from Shekou port in Shenzhen to Macau and to have it in hard copy with you at the time of landing.