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Derivatives 6a and 6b, have been obtained in a chemoselective manner by a two step synthesis from β-lapachone (3a) and nor-β-lapachone (3b), respectively, using CH2N2 in ether, which provided the lapachone-epoxide derivatives, 5a and 5b, followed by treatment with BF3.Et2O/CH2Cl2. Basic work-up of the reaction mixture of 5a or 5b with BF3.Et2O/CH2Cl2 led instead to isolation of the rearranged derivatives 7a and 7b, respectively. An ab initio theoretical study [B3LYP/6-311+G(d)] on 3a indicated that the carbon atom, C6, carries a higher positive charge than that at C5 and hence predicts a greater reactivity towards nucleophiles at C6. Another important factor controlling the chemoselectivity in the reaction of 3a with CH2N2 is the steric hindrance of the CH2 groups of the pyran ring.

Synthesis of new aldehyde derivatives from β-lapachone and nor-β-lapachone