Abstract
Aucubin, a natural iridoid widely extracted from Aucuba japonica presents a strong interest as semisynthetic raw substantial, thanks to its numerous features. In this study, we describe an unprecedented reaction between trimethylsilyldiazomethane and the aldehyde-derived aucubin (3a) leading to different original non-natural skeletons exemplified by the tricyclic compounds 6 and 9 (Figure 1). The influence of catalysts, solvents and temperature on the formation of the products together with the hydrolysis of enoxysilane 4 will be presented.
Highlights
Aucubin (1) is one of the most common and widespread iridoids of the plant kingdom. It has been isolated from many species belonging to more than ten plant families.[1]. It is very abundant in Aucuba japonica (Cornaceae), a common plant growing in temperate climate
Aucubin permitted the synthesis of various classes of biologically interesting chiral compounds: insect antifeedants,[17] carbocyclic nucleoside analogues,[18,19] aminocyclopentitol glycosidase inhibitors,[14] prostaglandins,[20]
We showed, for the first time, that the use of trimethylsilyldiazomethane (TMSDM) with -alkoxyenals allowed unexpectedly to a ring enlargement in one step of 3,4-dihydro-2H-pyran-5-carbaldehydes into trimethyl[(4E)-4,5,6,7tetrahydrooxepin-4-ylidenemethoxy]silanes.[16]
Summary
Aucubin (1) is one of the most common and widespread iridoids of the plant kingdom. It has been isolated from many species belonging to more than ten plant families.[1] It is very abundant in Aucuba japonica (Cornaceae), a common plant growing in temperate climate. It has been the first iridoid glucoside isolated in 1902 by E. Grimshaw in 1960,4 this naturally occurring material devoid of cytotoxic activity,[5,6,7] is used for several decades by organic chemists for the synthesis of chiral building blocks or scaffolds.[8,9,10,11,12,13,14,15,16] Aucubin permitted the synthesis of various classes of biologically interesting chiral compounds: insect antifeedants,[17] carbocyclic nucleoside analogues,[18,19] aminocyclopentitol glycosidase inhibitors,[14] prostaglandins,[20]
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