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Synthesis of a 2:3 mixture of dihydronepetalactones c and d. Reaction conditions: a) (COCl)2, DMSO, CH2Cl2, −70 °C to 0 °C (71%); b) p-TsOH, benzene, reflux (96%); c) NaBH4, MeOH, −20 °C; d) TBDMSCl, imidazole, DMF, 0 °C (78%) (over two steps); e) KOH, MeOH, rt (94%); f) RuCl3·3H2O (2 mol %), NaIO4, CCl4, CH3CN, phosphate buffer (pH 7), rt (69%); g) HF, CH3CN, rt (98%); h) DCC, DMAP, CH2Cl2 (62%).
