Total synthesis of the diazaphenanthrene alkaloid perlolidine

Powers, James C.; Ponticello, I. S.

doi:10.1021/ja01027a039

Cited by 26 publications

(2 citation statements)

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“…A título de exemplo apresentamos a síntese total da perlolidina 36 [34][35][36] (Esquema 17), um alcalóide isolado de um tipo de gramínea da Nova Zelândia. A ortolitiação da 2-fluorpiridina pelo LDA, seguida da adição de iodo dá acesso ao produto iodado 37 com um rendimento de 80%.…”

Section: Aplicações Sintéticasunclassified

Reações de ortometalacão em piridinas

Souza¹,

Almeida²

2002

Quím. Nova

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Recebido em 29/11/00; aceito em 2/5/01 THE ORTHO METALATION REACTION IN PYRIDINES. In this paper we describe a powerful methodology for the regiospecific construction of polysubstituted aromatic and heteroaromatic compounds. The DoM reaction (direct ortho-metalation) comprises the deprotonation in position ortho of a aromatic or heteroaromatic containing DMG (directed metalation group) by strong bases, normally an alkyllithium reagent, leading to an ortho-lithiated species. These species, upon treatment with electrophilic reagents, gives 1,2 disubstituted products.

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Section: Aplicações Sintéticasunclassified

Reações de ortometalacão em piridinas

Souza¹,

Almeida²

2002

Quím. Nova

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“…Endophyte‐infected tall fescue ( Festuca arundinacea Schreb., E+TF) is a primary forage species in pastures throughout the United States and is among the hardiest of cool‐season grasses. Endophyte‐infected tall fescue produces two types of alkaloids: those associated with the plant (Powers and Ponticello, 1968) and those due to the fungus Neotyphodium coenophialum (Porter, 1994), which lives symbiotically in the intercellular spaces of sheaths, stems, leaves, and seeds of tall fescue (Rottinghaus et al, 1991; Thompson et al, 2001).…”

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Plant Secondary Metabolites in Alfalfa, Birdsfoot Trefoil, Reed Canarygrass, and Tall Fescue Unaffected by Two Different Nitrogen Sources

et al. 2017

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Plant secondary metabolites (PSM) may increase the sustainability of agriculture systems by reducing inputs, as PSM protect plants against herbivores and pathogens, act as pesticides, insecticides, and anthelmintics while also attracting pollinators and seed dispersers. Therefore, it is important to understand what affects PSM fluctuation in plant tissues. Limited research has investigated how different nitrogen (N) sources affect PSM concentration in alfalfa (Medicago sativa L., Alf), birdsfoot trefoil (Lotus corniculatus L., BFT), reed canarygrass (Phalaris arundinacea L., RCG), and endophyte‐infected tall fescue (Festuca arundinacea Schreb., E+TF). We investigated how fecal manure (feces) and synthetic N fertilizer (urea, 46% H2NCONH2) influence N concentrations and the PSM ergovaline, gramine, saponins, and extractable condensed tannins (CT) in E+TF, RCG, Alf, and BFT, respectively. Ergovaline, saponins, and CT were not affected by fertilization. Gramine tended (P = 0.06) to be greater in control plots than in fertilized plots. Total N in E+TF and RCG was greater (P < 0.05) and tended to be greater for Alf (P = 0.08) in synthetically fertilized plots than in unfertilized plots. Seasonal variation in PSM and N was significant (P < 0.003) across all species and was species specific. Total N in E+TF was greatest in June (41.4 g kg−1), while ergovaline contents were at the lowest values recorded (117.2 μg kg−1), with subsequent increases to the greatest ergovaline values observed in July (680.0 μg kg−1). Our results reveal the variability in PSM production by plants and highlight the complexities of predicting fluctuations of PSM in forages. As environments where plants grow vary through space and time, we recommend studies on a case‐by‐case basis, depending on land management objectives.

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