Perbenzylated 1,7-dioxaspiro[5,5]undec-4-ene derivatives of sugars are obtained in three steps, starting from fully protected glycono-1,5-lactones. The procedure is based on the attack of a lithiated dithiinyl reagent (6) on the starting δ-glyconolactone. The C-glycosidation leads to the sole thermodynamically more stable α-hemiacetal derivative, the spirocyclization of which is then accomplished with BF3·Et2O. The fully protected unsaturated spiroacetals can be smoothly desulfurized for the purpose of any further elaborations of the free double bond.

Stereoselective synthesis of fully protected (S)-1,7-dioxaspiro[5,5]undec-4-ene derivatives of Sugars / Caputo, Romualdo; U., Ciriello; Festa, Pasquale; Guaragna, Annalisa; Palumbo, Giovanni; Pedatella, Silvana. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - (2003), pp. 2617-2621. [10.1002/ejoc.200300025]

Stereoselective synthesis of fully protected (S)-1,7-dioxaspiro[5,5]undec-4-ene derivatives of Sugars

CAPUTO, ROMUALDO;FESTA, PASQUALE;GUARAGNA, ANNALISA;PALUMBO, GIOVANNI;PEDATELLA, SILVANA
2003

Abstract

Perbenzylated 1,7-dioxaspiro[5,5]undec-4-ene derivatives of sugars are obtained in three steps, starting from fully protected glycono-1,5-lactones. The procedure is based on the attack of a lithiated dithiinyl reagent (6) on the starting δ-glyconolactone. The C-glycosidation leads to the sole thermodynamically more stable α-hemiacetal derivative, the spirocyclization of which is then accomplished with BF3·Et2O. The fully protected unsaturated spiroacetals can be smoothly desulfurized for the purpose of any further elaborations of the free double bond.
2003
Stereoselective synthesis of fully protected (S)-1,7-dioxaspiro[5,5]undec-4-ene derivatives of Sugars / Caputo, Romualdo; U., Ciriello; Festa, Pasquale; Guaragna, Annalisa; Palumbo, Giovanni; Pedatella, Silvana. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - (2003), pp. 2617-2621. [10.1002/ejoc.200300025]
File in questo prodotto:
Non ci sono file associati a questo prodotto.

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/11588/155838
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 18
  • ???jsp.display-item.citation.isi??? 15
social impact