Abstract
The asymmetric synthesis of a compound with the cyclopentan[c]pyran core of iridoid natural products in four steps and 40% overall yield is reported. Our methodology includes a one-pot tandem domino reaction which provides a trisubstituted cyclopentane with five new completely determined stereocenters, which were determined through 2D homo and heteronuclear NMR and n.O.e. experiments on different compounds specially designed for this purpose, such as a dioxane obtained from a diol. Due to their pharmaceutical properties, including sedative, analgesic, anti-inflammatory, CNS depressor or anti-conceptive effects, this methodology to produce the abovementioned iridoid derivatives, is an interesting strategy in terms of new drug discovery as well as pharmaceutical development.
Highlights
Iridoids are a very extensive family of secondary metabolites
We have demonstrated the use of chiral lithium (α-methylbenzyl)benzylamide (R)- or (S)-1) in transformations different domino reactions
We wanted to introduce an additional carbon atom in the α-position of the alkoxycarbonylmethyl group, so an electrophile was necessary after performing the abovementioned domino reaction in a tandem multicomponent reaction protocol
Summary
Iridoids are a very extensive family of secondary metabolites. They are found in both terrestrial and marine flora and fauna [1,2,3]. The genus Nepeta, with its bigger diversity located in the Mediterranean area, have demonstrated, in recent studies, that some extracts from different plants possess very interesting therapeutic properties, such as anti-inflammatory or analgesic effects, due to the abundant presence of nepetalactone derivatives [16,17]. This opens a promising researching area, since morphine use, nowadays, is responsible a lot of dependency and deaths.
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