A photoinduced reaction between diazoketones, isocyanides and silanols, followed by aldol dimerization of the resulting multicomponent adduct, affords polyfunctionalized 3,5-dihydroxypyrrolidin-2-one heterocycles in a straightforward manner. Six new bonds and two quaternary carbons are formed in just two steps with this complexity-generating methodology. A high degree of stereoselectivity is also observed, as a result of the mild conditions employed. Moreover, the 3,5-dihydroxypyrrolidin-2-one scaffold can be found in two families of biologically relevant natural products, namely anchinopeptolides and eusynstyelamides. The synthetic approach herein described appears to be a very convenient route for the preparation of their analogues.

Stereoselective Synthesis of 3,5-Dihydroxypyrrolidin-2-ones Through a Photoinduced Multicomponent Reaction Followed by Dimerization

Capurro P.;Lambruschini C.;Riva R.;Basso A.
2019-01-01

Abstract

A photoinduced reaction between diazoketones, isocyanides and silanols, followed by aldol dimerization of the resulting multicomponent adduct, affords polyfunctionalized 3,5-dihydroxypyrrolidin-2-one heterocycles in a straightforward manner. Six new bonds and two quaternary carbons are formed in just two steps with this complexity-generating methodology. A high degree of stereoselectivity is also observed, as a result of the mild conditions employed. Moreover, the 3,5-dihydroxypyrrolidin-2-one scaffold can be found in two families of biologically relevant natural products, namely anchinopeptolides and eusynstyelamides. The synthetic approach herein described appears to be a very convenient route for the preparation of their analogues.
File in questo prodotto:
File Dimensione Formato  
ejoc201901080.pdf

accesso chiuso

Tipologia: Documento in versione editoriale
Dimensione 831.99 kB
Formato Adobe PDF
831.99 kB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11567/973623
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 3
  • ???jsp.display-item.citation.isi??? 3
social impact