- Biomimetic-type synthesis of the racemic non-aromatic angucyclinones of the SF 2315 and SS 228Y types
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The biomimetic-type aldol reaction of the tricyclic (E)-configured precursors 6a/b gave the racemic nonaromatic angucycline derivatives 11-13 of the SF 2315 and SS 288Y types. Chelate controlled conditions in the cyclization of 6b led to the regioisomeric product 10.
- Krohn, Karsten,Floerke, Ulrich,Freund, Christian,Hayat, Nasir
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- Total Synthesis of (-)-Urdamycinone B through Polyketide Condensation
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(-)-Urdamycinone B, the enantiomer of a natural antitumor antibiotic, was synthesized by employing polyketide condensation reactions.
- Yamaguchi, Masahiko,Okuma, Tadashi,Horiguchi, Akira,Ikeura, Chinatsu,Minami, Toru
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Read Online
- A unified strategy for the syntheses of angucyclinone antibiotics: Total syntheses of tetrangulol, kanglemycin M, X-14881-E, and anhydrolandomycinone
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A unified strategy for the syntheses of angucyclinone antibiotics was developed utilizing sequential intramolecular enyne metathesis, Diels-Alder/aromatization, photooxygenation, and one-pot elimination/ aromatization reactions. The diversity in this sequ
- Vanga, Devendar Goud,Kaliappan, Krishna P.
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experimental part
p. 2250 - 2259
(2012/06/18)
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- Remote stereochemical control in asymmetric Diels-Alder reactions: Synthesis of the angucycline antibiotics, (-)-tetrangomycin and MM 47755
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The first asymmetric syntheses of the angucycline antibiotics, (-)-tetrangomycin and MM 47755, are achieved via a short efficient sequence starting from the chiral Lewis acid promoted Diels-Alder reaction of 5-hydroxy-1,4-naphthoquinone and (±)-(E)-5-dimethylphenylsilyl-5-methyl-1-(2′- trimethylsiloxyvinyl)cyclohexene 7 where an effective kinetic resolution of the latter, controlled by its remote stereocentre, is described.
- Landells, John S.,Larsen, David S.,Simpson, Jim
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p. 5193 - 5196
(2007/10/03)
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- Synthesis of angucyclines. 8. Biomimetic-type synthesis of rabelomycin, tetrangomycin, and related ring B aromatic angucyclinones
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The angucyclinones with aromatic ring B (1a-c and 2a-c) are prepared in a biomimetic-type synthesis by two successive aldol cyclizations starting from the substituted naphthoquinones 12a-c. In both cyclization steps the C-H acidity of the potential nucleophilic centers determines the mode of cyclization under kinetically controlled conditions. The tetrahydroanthraquinones 13a-c/14a-c are hydroxylated at C-4 to the phenolic anthraquinones 16a-c upon treatment with excess NMO.
- Krohn, Karsten,Boeker, Norbert,Floerke, Ulrich,Freund, Christian
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p. 2350 - 2356
(2007/10/03)
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- Total Synthesis of Angucyclines, 4. Synthesis of rac-Tetrangomycin
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The synthesis of racemic tetrangomycin (11) is reported.In the key step the hexahydrobenzanthraquinone 8 is generated in a regioselective Diels-Alder reaction of diene 5 with bromonaphthoquinone 7.The conversion of 8 into 11 involves only three operati
- Krohn, Karsten,Khanbabaee, Karamali
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p. 1109 - 1112
(2007/10/02)
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