1998
DOI: 10.1021/jo9807868
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Oxidative Intramolecular Phenolic Coupling Reaction Induced by a Hypervalent Iodine(III) Reagent:  Leading to Galanthamine-Type Amaryllidaceae Alkaloids

Abstract: By extending our oxidative phenol-coupling reactions using a hypervalent iodine(III) reagent, a versatile synthetic procedure for the galanthamine-type Amaryllidaceae alkaloids was accomplished. The first total synthesis of (±)-sanguinine and the total syntheses of (±)-galanthamine, (±)-narwedine, (±)-lycoramine, and (±)-norgalanthamine were also successfully carried out.

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Cited by 159 publications
(50 citation statements)
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“…15) The concentrated EtOAc layer (16 g) was subjected to column chromatography over silica gel and eluted with a gradient of i-Pr 2 O-MeOH (5 : 1 to pure MeOH) to give nine fractions. Purification of fraction 2 by silica gel column with CHCl 3 -MeOH (9 : 1) furnished daidzein (2 mg), 32) protocatechuic acid (6 mg), 33) protocatechuic acid methyl ester (11 mg), 34) 4-hydroxybenzoic acid (5 mg), 9) and pcoumaric acid (1 mg). 9) Further separation of fraction 3 on silica gel column with a gradient of CHCl 3 -MeOH (9 : 1 to pure MeOH) yielded begonanline (1, 5 mg), methyl (S)-glycerate (3, 9 mg), and (Ϫ)-catechin (13, 998 mg).…”
Section: )mentioning
confidence: 99%
“…15) The concentrated EtOAc layer (16 g) was subjected to column chromatography over silica gel and eluted with a gradient of i-Pr 2 O-MeOH (5 : 1 to pure MeOH) to give nine fractions. Purification of fraction 2 by silica gel column with CHCl 3 -MeOH (9 : 1) furnished daidzein (2 mg), 32) protocatechuic acid (6 mg), 33) protocatechuic acid methyl ester (11 mg), 34) 4-hydroxybenzoic acid (5 mg), 9) and pcoumaric acid (1 mg). 9) Further separation of fraction 3 on silica gel column with a gradient of CHCl 3 -MeOH (9 : 1 to pure MeOH) yielded begonanline (1, 5 mg), methyl (S)-glycerate (3, 9 mg), and (Ϫ)-catechin (13, 998 mg).…”
Section: )mentioning
confidence: 99%
“…Next, the PIFA-mediated intramolecular phenol couplings of 7a and 7b were attempted and were found to afford good yields (75 and 95%, respectively) of dienone (11a, b) when the reaction was carried out at Ϫ40°C in trifluoroethanol, where low nucleophilicity is believed to increase in the chemical yield of the oxidative coupling (Chart 1). [33][34][35][36][37] Herein, we were able to show that the use of the PIFA-mediated phenol coupling, where the substrates had a tri-Omethyl pyrogallol ring instead of a catechol moiety in the norbelladine skeleton, could provide an excellent method for the synthesis of 1. However, the attempted demethylation of 11a and 11b with boron tribromide at Ϫ78°C to afford tetrahydrodibenzofuran derivatives (8a, b) was unsuccessful because of difficulties in the selective cleavage of methyl ethers and the occurrence of side-reactions such as dienonephenol rearrangement.…”
Section: Resultsmentioning
confidence: 95%
“…Reductive amination of 14a with tyramine in the presence of sodium borohydride and successive treatment of the product 12b with trifluoroacetic anhydride produced a good yield of trifluoroacetamide 12a. However, solubility of 12a in trifluoroethanol, the most suitable solvent for PIFA-mediated reaction, [33][34][35][36][37] was quite poor and the reaction attained in trifluoroacetic acid produced a low yield (12%) of 8a probably due to sidereactions triggered by the generation of a radical species on the pyrogallol moiety.…”
Section: Resultsmentioning
confidence: 99%
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