Multicomponent Domino Reaction in the Asymmetric Synthesis of Cyclopentan[c]pyran Core of Iridoid Natural Products

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 stereocente...

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Bibliographic Details
Published inMolecules (Basel, Switzerland) Vol. 25; no. 6; p. 1308
Main Authors Manchado, Alejandro, Ramos, Victoria Elena, Díez, David, Garrido, Narciso M
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 13.03.2020
MDPI
Subjects
Analgesics
asymmetric aza-michael addition
asymmetric domino reaction
Asymmetric synthesis
Asymmetry
Benzaldehydes - chemistry
Biological Products - chemical synthesis
Biological Products - chemistry
Carbon-13 Magnetic Resonance Spectroscopy
Cascade chemical reactions
chiral lithium amide
cyclopentan[c]pyran
Cyclopentane
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Hydrogen
Inflammation
iridoid
Iridoids - chemical synthesis
Iridoids - chemistry
multicomponent reaction
Natural products
nepetalactone
Oxidation-Reduction
Pharmaceuticals
Proton Magnetic Resonance Spectroscopy
Pyrans - chemical synthesis
Pyrans - chemistry
Stereoisomerism
cyclopentan[c]pyran
asymmetric domino reaction
nepetalactone
iridoid
multicomponent reaction
asymmetric aza-Michael addition
chiral lithium amide
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Summary: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules25061308