Beta-ionone synthesis using anhydrous hydrogen fluoride

Markovich, Yu. D.; Panfilov, A. V.; Zhirov, A. A.; Kirsanov, A. T.; Gorbach, L.A.; Taraskin, K. A.

doi:10.1007/bf02465747

Cited by 3 publications

(2 citation statements)

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“…609 The synthesis of β-ionone 525 from pseudoionone 527 can be accomplished by treating the latter with ten equivalents of HF in petroleum ether containing catalytic amounts of KF. 610 Alternatively, pseudoionone 527 can be isomerised to α-ionone 526 by treatment with trifluoroacetic acid, and 526 can then be further isomerised to β-ionone 525 by sulfuric acid. 611 The utilisation of enantioselective protonation procedures in relation to the synthesis of (S)-(Ϫ)-damascone 528 has been reviewed.…”

Section: Thujanesmentioning

confidence: 99%

Monoterpenoids (mid-1997 to mid-1999)

Grayson

2000

Nat. Prod. Rep.

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In situ RNA hybridization and immunocytochemistry were used to establish the cellular distribution of monoterpenoid indole alkaloid biosynthesis in Madagascar periwinkle (Catharanthus roseus). Tryptophan decarboxylase (TDC) and strictosidine synthase (STR1), which are involved in the biosynthesis of the central intermediate strictosidine, and desacetoxyvindoline 4-hydroxylase (D4H) and deacetylvindoline 4-O-acetyltransferase (DAT), which are involved in the terminal steps of vindoline biosynthesis, were localized. tdc and str1 mRNAs were present in the epidermis of stems, leaves, and flower buds, whereas they appeared in most protoderm and cortical cells around the apical meristem of root tips. In marked contrast, d4h and dat mRNAs were associated with the laticifer and idioblast cells of leaves, stems, and flower buds. Immunocytochemical localization for TDC, D4H, and DAT proteins confirmed the differential localiza-tion of early and late stages of vindoline biosynthesis. Therefore, we concluded that the elaboration of the major leaf al-kaloids involves the participation of at least two cell types and requires the intercellular translocation of a pathway intermediate. A basipetal gradient of expression in maturing leaves also was shown for all four genes by in situ RNA hy-bridization studies and by complementary studies with dissected leaves, suggesting that expression of the vindoline pathway occurs transiently during early leaf development. These results partially explain why attempts to produce vin-doline by cell culture technology have failed. INTRODUCTION The organs forming the plant body consist of several different cell types that are organized in relation to each other and that confer specific functions to the resulting organ. Each cell type emerges from an undifferentiated meristem according to a sophisticated and partially understood developmental program (Sylvester et al., 1996; von Arnim and Deng, 1996). The commitment to differentiate into specialized structures involves the perception by cells in the meristem of a complex array of signals, which communicate cellular age, position in relation to other cells, and hormonal balance. Environmental factors, such as light and temperature, also play a critical role in modulating these signals throughout the process of organogenesis (Bernier, 1988; Dale, 1988; Sylvester et al., 1996). In addition to morphogenesis, developmental processes result in biochemical specialization of cells for the biosyn-thesis and/or accumulation of secondary metabolites, such as phenylpropanoids (Ibrahim et al.

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