- Unified synthesis and cytotoxic activity of 8-O -methylfusarubin and its analogues
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A simple and unified synthesis of four related pyranonaphthoquinone natural products, e.g. 8-O-methylfusarubin, 8-O-methylanhydrofusarubin, fusarubin and anhydrofusarubin, is reported. The key synthetic features include the precedented Diels-Alder cycload
- Vijitphan, Pongsit,Rukachaisirikul, Vatcharin,Muanprasat, Chatchai,Iawsipo, Panata,Panprasert, Jiraporn,Tadpetch, Kwanruthai
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p. 7078 - 7087
(2019/08/01)
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- The synthesis of the pyranonaphthoquinones dehydroherbarin and anhydrofusarubin using Wacker oxidation methodology as a key step and other unexpected oxidation reactions with ceric ammonium nitrate and salcomine
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The synthesis of two closely related pyranonaphthoquinones, dehydroherbarin and anhydrofusarubin, is described. The construction of the naphthalene nuclei was achieved using the Stobbe condensation reaction using 2,4- dimethoxybenzaldehyde and 2,4,5-trime
- Pillay, Adushan,Rousseau, Amanda L.,Fernandes, Manuel A.,De Koning, Charles B.
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p. 7809 - 7819
(2013/04/23)
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- Use of 13C in biosynthetic studies. The labeling pattern in dihydrofusarubin enriched from - and acetate in cultures of Fusarium solani.
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The pattern of 13C and 2H incorporation from -, -, 0;1;1,2-13C1;0;1>-, and 0;1,2-2H3;3>acetate into dihydrofusarubin 1, produced by cultures of Fusarium solani, has been determined by 13C and 2H nmr of the derivatives anhydrofusarubin 3 and anhydrofusarubin diacetate 4.The results show that 1 is biosynthesized from seven uniformly-incorporated acetate units with C-3, C-11 originating from the starter unit.They strongly suggest that linear head-to-tail condensation of an acetate and six malonate units forms a single-chain heptaketide intermediate.The evidence also suggests that, during conversion of -labeled acetyl-CoA to malonyl-CoA, 2H is transferred to biotin carboxyl carrier protein where it does not exchange rapidly with medium and is available for conversion of endogenous malonyl-CoA to -enriched acetyl-CoA.
- Kurobane, Itsuo,Vining, Leo C.,McInnes, A. Gavin,Walter, John A.
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p. 1380 - 1385
(2007/10/02)
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