Hydroxylation Of Dipterocarpol Compounds In Dipterocarpus Alatus By Chemical Transformations

Abstract

The topic was to perform hydroxylation of the dipterocarpol and lactone – dipterocarpol to obtain the most polar compound. Lactone was synthesized from dipterocarpol obtained roundly 64.45%. Meanwhile, dipterocarpol was extracted only about 15% because of high impurities and loss during crystallization and recrystallization stages. Also, dipterocarpol processed to alcohol and alkene derivatives’ formation totally with a high yield which was 95.59% and 78.78%, respectively, and the hydroxylation step was also successful. However, due to three double bonds on dipterocarpol’ structure, the selectivity for the desired product was hard to isolate. On the contrary, about the lactone case, lactone reduced into two alcohols at the first step because of its structure, but the yield was not expected as in dipterocarpol’s case (37.37%) due to loss during workup stage. In the dehydration step, only one alkene was formed led to a yield of 75.25%. During the hydroxylation step, lactone, which gave a new compound that had one hydroxyl group and one ester group with the mCPBA ring, was a good sign in producing a more polar compound than dipterocarpol. Nevertheless, the yield was low at around 17.65% due to impurities. All of the synthesized compounds’ structures are corresponding to the structures shown in 1H NMR and 13C NMR spectra.