The first question I would like to ask about the circuit (as drawn now): Is the node marked as "-300V" really 300V below 0V (0V is the ground node), or is it just the name given to the negative terminal of the 300VDC supply? It would greatly help to show how the nodes marked "+300V", "-300V, and "+15V" are related to the reference node ("0V", ie: the ground symbol).
The next question is: what are the identifiers for each of the components? None of the components can be identifed by a simple string, eg: "R1", or "Q1". This makes it very difficult for anyone trying to help you, since we cannot easly refer to a partuclar commpionent on your diagram. For example, "Q1" is much easier and clearer than writing: "the left-most MOSFET with its drain connected to the +300V node".
To try to assist you with this: For an inexperienced designer, I recommend not trying to design your own "home-brew discrete boot-strap" circuit for an application where the main power supply rails are more than about 50V above or below the control circuit (ground). There are just too many details and things that can go wrong with boot-straps operating over 50V above the control circuit, and the higher the voltage the more issues there are to worry about.
Instead, I would recommned using a more complete solution, such as:
A commercially available solution using the bootstrap technique, for example:
https://www.digikey.com.au/en/products/detail/infineon-technologies/IR2110PBF/811566
https://au.mouser.com/datasheet/2/472/si823x_datasheet-3084970.pdf
https://rocelec.widen.net/view/pdf/ttqyaoj0x5/ANDIS03903-1.pdf?t.download=true&u=5oefqw
Using an IC designed to work with isolation transformers, eg:
https://www.st.com/resource/en/application_note/an461-an-isolated-gate-drive-for-power-mosfets-and--igbts-stmicroelectronics.pdf
There are many resources to explain the various design considerations of gate drivers for high-voltage (>50V) applications, here is just one example:
https://www.onsemi.com/pub/collateral/tnd379-d.pdf