Biomimetic syntheses of pretetramides.  3.  Synthesis of 6-methylpretetramides using a preassembled D ring template

Harris, Thomas M.; Harris, Constance M.; Kuzma, Peter C.; Lee, J. Y.-C.; Mahalingam, Sankaran; Gilbreath, S. G.

doi:10.1021/ja00226a038

Cited by 17 publications

(6 citation statements)

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“…Compound 3 was previously reported as a synthetic product in the synthesis of key intermediates for mycophenolic acid, 20 in the selective nuclear lithiation of aromatic compounds, 21 and in the synthesis of pretetramides. 19 It is of unknown toxicity and is reported here for the first time as a fungal metabolite. The configuration at C-3 was not reported.…”

Section: Resultsmentioning

confidence: 90%

“…The data agree with the literature values and are consistent with the structure for 5,7-dimethoxy-3-methylpthalide. 19,20 The 13 C chemical shift assignments are reported for the first time (Table 2). Compound 3 was previously reported as a synthetic product in the synthesis of key intermediates for mycophenolic acid, 20 in the selective nuclear lithiation of aromatic compounds, 21 and in the synthesis of pretetramides.…”

Section: Resultsmentioning

confidence: 99%

“…(3R)-5-Methylmellein. 3,4-Dihydro-(3R),5-dimethyl-8-hydroxyisocoumarin (7): 1 H NMR (CDCl3, 400 MHz) δ 11.02 (s, 1H, OH), 7.31 (d, J ) 8.5 Hz, 1H), 6.84 (d, J ) 8.5 Hz, 1H), 4.70 (m, 1H), 2.97 (dd, J ) 16.7 Hz, J ) 3.4 Hz, 1H), 2.74 (dd, J ) 16.6 Hz, J ) 11.5 Hz, 1H), 2.21 (s, 3H), 1.57 (d, J ) 6.1 Hz); EIMS m/z 192 [M] + (100), 174 (17), 163 (25), 148 (19); HRMS m/z 192.0793 (calcd for C 11H12O3, 192.0787).…”

Section: Methodsmentioning

confidence: 99%

“…(3R)-Mellein. 3,4-Dihydro-(3R)-methyl-8-hydroxyisocoumarin (8): 1 H NMR (CDCl3, 400 MHz) δ 11.04 (s, OH), 7.41 (dd, J ) 8.2 Hz, J ) 7.6 Hz, 1H), 6.89 (d, J ) 8.4 Hz, 1H), 6.69 (dd, J ) 7.4 Hz, J ) 1.0 Hz, 1H), 4.74 (sextet, J ) 6.4 Hz, 1H), 2.93 (d, J ) 6.8 Hz, 2H), 1.53 (d, J ) 6.0 Hz, 3H); EIMS m/z 178 [M] + (59), 160 (20), 149 (15), 134 (37), 61 (19), 45 (16), 43 (100), 29 (16); HRMS m/z 178.0638 (calcd for C 10H10O3, 178.0630).…”

Section: Methodsmentioning

confidence: 99%

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Characterization of Polyketide Metabolites from Foliar Endophytes of Picea glauca

et al. 2008

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A collection of 250 foliar endophytes of Picea glauca (white spruce) yielded several isolates that produced metabolites toxic to Choristoneura fumiferana (spruce budworm). Three of these strains were selected for further study based on their ability to be cultured and produce secondary metabolites under laboratory conditions. The culture filtrate of each was extracted and analyzed by LC-MS and LC-NMR, and the major metabolites were isolated and characterized. Structures were elucidated by spectroscopic analyses including 2D NMR and HRMS and by comparison to literature data. In some cases the extract was methylated in order to facilitate separation, but the original natural structure was determined by comparing the NMR data of the isolated methylated product with that of the stop-flow NMR of the underivatized extract (i.e., 2a, 2b, and 4). Two of these metabolites, 1 and 2a, are new structures, 3 and 4 are reported here for the first time as fungal metabolites, and 5- 10 as known fungal metabolites from other species. Tyrosol (10) was the only common metabolite found in all three extracts but did not account for the observed toxicity to C. fumiferana.

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Section: Resultsmentioning

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Characterization of Polyketide Metabolites from Foliar Endophytes of Picea glauca

et al. 2008

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“…3 Another dimethoxyphthalide 2 has been reported from Albizzia jubrissin. 4 These phthalides are valuable as they possess significant biological properties 5,6 and also are widely accepted synthons for the construction of various types of polycyclic systems 7 including isocoumarins, 8 anthraquinones, 9 anthracycline antibiotics, 10 lignans, 11 etc. The phthalides 1b and 1e, for example, are potential precursors of mycophenolic acid (MPA) 3, an important antiparasitic, 12 antineoplastic 13 and antiviral 14 agent, in a synthesis involving a stereospecific orthoester Claisen rearrangement.…”

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confidence: 99%