Synthetic Approaches to the Angucycline Antibiotics: A Synthesis of (±)-Hatomarubigin B and C.
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The synthesis of the angucycline natural products hatomarubigin B and C in racemic form is described. The key step in the construction of the benz[a]anthraquinone skeleton of these molecules was the Diels–Alder reaction of the acetate of (E,1R*,5R*)-3-(2′-methoxyvinyl)-5-methylcyclohex-2-en-1-ol and 5-acetoxy-8-hydroxy-1,4-naphthoquinone. Methylation of the C11 phenolic group of the resulting cycloadduct, followed by aromatization of the B ring with subsequent deacylation gave (±)-hatomarubigin C. Oxidation of the latter compound with Dess-Martin periodinane, 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one, gave (±)-hatomarubigin B.
2016 ◽
Vol 20
(22)
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pp. 2421-2442
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2018 ◽
Vol 15
(2)
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pp. 221-229
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1985 ◽
Vol 50
(20)
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pp. 3738-3749
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2000 ◽
Vol 58
(1)
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pp. 39-49
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