An Efficient Method for Preparation of Chiral Arylmenthol Glyoxylates

Blanco, José M.; Caamaño, Olga; Fernández, Fernando Nieto; Garcı́a-Mera, Xerardo; López, Carmen; Rodríguez‐Borges, José E.; Hergueta, Antonio R.

doi:10.1055/s-1998-2198

Cited by 7 publications

(1 citation statement)

References 11 publications

(16 reference statements)

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“…401 Reduction of the acid chloride 203 by tributyltin hydride affords the chiral 8-phenylmenthyl glyoxalate 204. 402 Asymmetric aldol reactions between benzyloxyacetaldehyde and the ketene acetal 205 which are catalysed by the chiral Lewis acid 206 are remarkably temperature dependent. 403 Thus, at Ϫ78 ЊC the product is (ϩ)-207 of 98% ee whereas at Ϫ30 ЊC (Ϫ)-207 of 85% ee is formed.…”

Section: Menthanesmentioning

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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Section: Menthanesmentioning

confidence: 99%

Monoterpenoids (mid-1997 to mid-1999)

Grayson

2000

Nat. Prod. Rep.

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Synthetic Uses ofR₃MH(M = Ge,Sn,Pb)

Carland

Schiesser

2009

Patai's Chemistry of Functional Groups

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Introduction The Preparation of Novel Trialkylgermanes and Stannanes Trialkyltin Hydrides as Reagents in Radical Chain Reactions Trialkyltin Hydrides in Non‐Radical Chemistry Trialkylgermanium and Lead Hydrides in Synthesis Acknowledgement

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