Abstract
AbstractKey steps in the synthesis of derivatives of the angucycline, tetrangulol include the use of a palladium catalyzed Suzuki‐Miyaura cross‐coupling reaction for the assembly of 2‐(1,4‐dimethoxy‐3‐(2‐methylprop‐1‐en‐1‐yl)naphthalen‐2‐yl)‐3‐methoxy‐5‐methylbenzaldehyde from 2‐iodo‐3‐methoxy‐5‐methylbenzaldehyde and 2‐(1,4‐dimethoxy‐3‐(2‐methylprop‐1‐en‐1‐yl)naphthalen‐2‐yl)‐4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolane. The biaryl product was then subjected to an iron‐catalyzed ring‐closing carbonyl‐olefin metathesis reaction to afford 1,7,12‐trimethoxy‐3‐methyltetraphene, which was oxidized to the corresponding quinone. Late stage oxidation of the quinone with Ru[Cl2(p‐cymene)]2 and an oxidant unexpectedly afforded the chlorinated compounds, 2,4‐dichloro‐11‐hydroxy‐1‐methoxy‐3‐methyltetraphene‐7,12‐dione and 2,4‐dichloro‐6‐hydroxy‐1‐methoxy‐3‐methyltetraphene‐7,12‐dione.
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