1984
DOI: 10.1055/s-2007-969647
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Chemistry of Acronycine VI. Proton NMR Spectral Assignments of Acronycine and Derivatives and the Formation of Isonoracronycine

Abstract: Proton NMR assignments for acronycine and a series of derivatives are reported based on extensive homonuclear decoupling and nOe experiments at high-field. The formation of isonoracronycine ( 3) from noracronycine ( 2) under acidic conditions is discussed.

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Cited by 10 publications
(17 citation statements)
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References 20 publications
(38 reference statements)
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“…When noracronycine (2) was treated with a mixture of 98% H2S04 and MeOH in the ratio 1:1, the yield of was about 40%, a tenfold increase compared with 98% H2S04. Catalytic hydrogenation of 3 afforded dihydro AB-1 (9) in almost quantitative yield (11). As reported previously (14), dihydro AB-1 (9) could also be produced, in about 40% yield, through a condensation-disproportionation reaction together with dihydro AB-3 (13), by treating a 1:10 mixture of AB-1 (3) and dihydronoracronycine (6) with methanolic HC1 under a N2 atmosphere at room temperature for 24 h.…”
supporting
confidence: 66%
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“…When noracronycine (2) was treated with a mixture of 98% H2S04 and MeOH in the ratio 1:1, the yield of was about 40%, a tenfold increase compared with 98% H2S04. Catalytic hydrogenation of 3 afforded dihydro AB-1 (9) in almost quantitative yield (11). As reported previously (14), dihydro AB-1 (9) could also be produced, in about 40% yield, through a condensation-disproportionation reaction together with dihydro AB-3 (13), by treating a 1:10 mixture of AB-1 (3) and dihydronoracronycine (6) with methanolic HC1 under a N2 atmosphere at room temperature for 24 h.…”
supporting
confidence: 66%
“…int.) 616 (M+, 46), 601(16), 598 (15), 587 (12), 318 (10), 311 (15), 310(68), 309(26), 308(48), 307 (100), 306 (10), 292 (31), 280 (22), 278(26), 264 (12), 263 (13), 262(18), 254(19), and 236 (9).…”
Section: Syntheses Of Dihydrounclassified
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“…This synthetic method has now been applied to a variety of hemiterpenoid quinoline alkaloids. Thus the 4-hydroxylated carboxylic acids (42) behave similarly, to give a mixture of the prenylated derivatives ( 43) and ( 45 form the isopropylfuroquinoline (52) ; the latter compound was also prepared by successive reactions of compound (48) with Nbromosuccinimide and formic acid.30 A new synthesis of the alkaloid lunacrine (51) resulted from catalytic reduction of the isopropylfuroquinoline (52) followed by the reaction of the product with methyl iodide and rearrangement of the resultant quaternary ammonium salt, using the method that was described previously. Grundon et ~1 .…”
Section: Non-terpenoid Quinolinesmentioning
confidence: 99%