Synthesis of saframycins. IX. An efficient synthesis of the ABC ring of safracins

Article abstract of DOI:10.1016/S0040-4020(01)89667-8

1,2,3,4,5,6-Hexahydro-10-hydroxy-1,5-imino-9-methoxy-3,8,11-trimethyl- 3-benzazocine 3b embodying all of the skeletal features of the ABC ring of safracins has been synthesized from compound 4a via a direct regioselective bromination, followed by the sequence reduction, metal-halogen interchange, and reaction of the organometallic intermediate with nitrobenzene. And the conversion of 3b to a quinone 21b is also described.