From citronellal to iridoids: asymmetric synthesis of iridoids and their analogues via organocatalytic intramolecular Michael reactions

A series of iridoids, including iridomyrmecin A, B, C', D', (-)-isoiridomyrmecin, (+)-7- -boschnialactone, and the inside-yohimbine analogues have been synthesized from readily available, naturally occurring (-)-citronellal the key step reaction of metathesis, organocatalysis, and subseque...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2023-05, Vol.21 (20), p.4200-4205
Main Authors: Tammisetti, Raviramanujayya, Chaudhari, Prakash D, Hong, Bor-Cherng, Chien, Su-Ying
Format: Article
Language:English
Subjects:
Acetic acid
Aldehydes
Alkylation
Asymmetric synthesis
Catalysts
Citronellal
Crystallography
Metathesis
Michael reaction
Single crystals
Stereoselectivity
Yohimbine
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Summary:A series of iridoids, including iridomyrmecin A, B, C', D', (-)-isoiridomyrmecin, (+)-7- -boschnialactone, and the inside-yohimbine analogues have been synthesized from readily available, naturally occurring (-)-citronellal the key step reaction of metathesis, organocatalysis, and subsequent transformations, such as reduction, lactonization, alkylation, Pictet-Spengler reaction and lactamization. Notably, the use of DBU as an additive in the organocatalytic intramolecular Michael reaction of an aldehyde ester with Jørgensen-Hayashi catalysts resulted in better stereoselectivity than the conditions using acetic acid as an additive. The structures of three products have been unequivocally established with single-crystal X-ray crystallographic analyses.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob00439b