Beilstein J. Org. Chem.2022,18, 754–768, doi:10.3762/bjoc.18.76
formation of hydrazone 28. As one equivalent of water is formed in this condensation process, which is detrimental for the subsequent Shapiroreaction, water is continuously removed by in-line separation of the reaction mixture using a PTFE-membrane separator. The organic layer is then mixed with a solution
of n-butyllithium in hexanes to initiate the Shapiroreaction of hydrazone 28 proceeding supposedly via dilithiated intermediate 29. As the nitrogen produced in the reaction increases the volume of the reaction mixture and therefore is drastically shortening the residence time, a cooled glass column
) via selective hydrogenation to enone 27, condensation to hydrazone 28 and subsequent Shapiroreaction. DMPS = dimethylpolysilane-modified platinum catalyst; Ts = tosyl.
Selective hydrogenation of alkyne 31 to “leaf alcohol” 32 employing a solid-supported palladium catalyst.
A) Synthesis of jasmonal
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Graphical Abstract
Figure 1:
The olfactory spectrum wheel ordering different types of odorants from fruity to musky.
Beilstein J. Org. Chem.2016,12, 1127–1135, doi:10.3762/bjoc.12.109
-Sud, 5, rue Jean-Baptiste Clément, 92296 Châtenay-Malabry, France 10.3762/bjoc.12.109 Abstract The synthesis of ω-di-(trideuteromethyl)-trisnorsqualenic acid has been achieved from natural squalene. The synthesis features the use of a Shapiroreaction of acetone-d6 trisylhydrazone as a key step to
: deuterium labelling; nanomedicine; Raman spectroscopy; Shapiroreaction; squalene; Introduction
Application of nanotechnology to medicine holds promises to profoundly impact healthcare especially to treat severe diseases such as cancer, intracellular infections, neurodegenerative diseases, etc. Indeed, the
[36]. Having secured an efficient method to reinstall the isopropylidene end-group, we turned our attention to the application of this method to a two-end functionalized squalene derivative. However, when applied to dialdehyde 5 the Shapiroreaction led to a mixture of starting material (30%), allylic
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Graphical Abstract
Figure 1:
Structure of squalenic acid-d6, gemcitabine and GemSQ-d6 conjugate.