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Synthesis of the A-ring acid chloride (14) from ortho-vanillin (15). Reagents and conditions: i. Br2, NaOAc, AcOH, rt; ii. H2O2, NaOH, H2O, 0 °C (83% yield from 15); iii. CH2I2, K2CO3, DMF, 80 °C (74% yield); iv. SnCl4, CH3OCHCl2, DCM, −78 °C (66% yield); v. Na2HPO4.H2O, NaClO2, 2-methyl-2-butene, tBuOH:H2O (5:1), rt (92% yield); vi. (COCl)2, DMF, DCM, rt (not purified).
