This paper reports a 10 step synthesis of 4-HO-5-MeO-DMT from  ortho-vanillin. Alexander Shulgin hypothesized that 4-HO-5-MeO-DMT could be biosynthesized by feeding Psilocybe cultures with 5-MeO-DMT, referencing a 1988 study by Jochen Gartz where transformation of DET into 4-HO-DET and 4-PO-DET was reported using such a method, with neither compounds having ever been found in nature.
This paper explores the synthesis of 4-HO-5-MeO-DMT from ortho-vanillin, a method proposed by Alexander Shulgin and supported by Jochen Gartz's research on DET transformation. The study highlights the potential for natural production through Psilocybe cultures but also notes that neither compound has been found in nature.