Synthesis of balsaminone A, a naturally occurring pentacyclic dinaphthofuran quinone |
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Authors: | Padwal Jalindar Lewis William Moody Christopher J |
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Affiliation: | School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK. |
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Abstract: | A short synthesis of the natural product balsaminone A, a dinaphthofuran quinone, is described. The key steps of the synthesis are base-induced coupling of 1,4-dihydroxy-2-naphthaldehyde with 2,3-dichloronaphthoquinone to give a pentacyclic dinaphthofuran directly, followed by conversion of the aldehyde into the desired methoxy group via the corresponding phenol. The synthesis, in which the structure of a key pentacyclic intermediate is corroborated by X-ray crystallography, confirms the original structural assignment of the natural product. |
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