Sum values with latest dates per year

hello all,

i have the below data

             6/30/2020 - 12/31/2020 - 6/30/2021 - 12/31/2021 - 6/30/2022
Item 1     $100               $150             $200              $250            $300
Item 2      $200              $250              $300              $350            $400

and i would like to sum the data per yeat but:

1) to take in consideration the latest data (meaning December)

2) if there is no data for December like in 2022 then to take the previous meaning 06/30/22.

this is the outcome i would like:

thank you in advance.