Formal synthesis of the juglomycins

Abstract

5′-Deoxyjuglomycin A 3 and 5′-methoxyjuglomycin A 4 have been synthesized via oxidative fragmentation of furo[3,2-b]naphtho[2,1-d]furans 9 and 10 respectively. Addition of 2-trimethylsiloxyfuran 5 to naphthoquinone sulfides 7, 8 afforded the key adducts 9, 10 which then underwent fragmentation to the quinone sulfides 11, 14 using ceric ammonium nitrate. Treatment of the trimethylsilyl derivatives 13, 15 of the sulfides 11, 14 with meta-chloroperoxybenzoic acid effected conversion into the sulfoxides 16, 18 which then underwent smooth desulfurization using tributyltin hydride to the quinones 21, 23. Finally, hydrolysis of the trimethylsilyl group completed the synthesis of 5′-deoxyjuglomycin A 3 and 5′-methoxyjuglomycin A 4.