Use of (S)-trans-gamma-Monocyclofarnesol as a Useful Chiral Building Block for the Stereoselective Synthesis of Diterpenic Natural Products (Articolo in rivista)

Type

• Articolo in rivista (Classe)
• Prodotto della ricerca (Classe)

Label

• Use of (S)-trans-gamma-Monocyclofarnesol as a Useful Chiral Building Block for the Stereoselective Synthesis of Diterpenic Natural Products (Articolo in rivista) (literal)

Anno

• 2014-01-01T00:00:00+01:00 (literal)

Alternative label

• Serra, Stefano; Cominetti, Alessandra A.; Lissoni, Veronica (2014)
  Use of (S)-trans-gamma-Monocyclofarnesol as a Useful Chiral Building Block for the Stereoselective Synthesis of Diterpenic Natural Products
  in Natural product communications
  (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

• Serra, Stefano; Cominetti, Alessandra A.; Lissoni, Veronica (literal)

Pagina inizio

• 329 (literal)

Pagina fine

• 335 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

• 9 (literal)

Rivista

• Natural product communications (Rivista)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali

• 7 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo

• 3 (literal)

Note

• ISI Web of Science (WoS) (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

• Consiglio Nazionale delle Ricerche (CNR); University of Milan (literal)

Titolo

• Use of (S)-trans-gamma-Monocyclofarnesol as a Useful Chiral Building Block for the Stereoselective Synthesis of Diterpenic Natural Products (literal)

Abstract

• A comprehensive study of the exploitation of (S)-trans-gamma-monocyclofarnesol as a useful chiral building block for the stereoselective synthesis of natural diterpene derivatives is here described. The farnesol derivative (+)-1 was used as starting material in the preparation of the diterpenes (S)-dehydroambliol-A and (S)-trixagol, as well as for the syntheses of the dinorditerpene (S)-dinortrixagone and of the guanidine-interrupted terpenoid (S)-dotofide. Key steps of the presented syntheses were the cross-coupling between an allyl acetate and a Grignard reagent, the Wittig reaction, the selective preparation of a diacylguanidine derivative and the alkylation of a sulfone derivative, followed by the reductive removal of the same functional group. It is worth noting that the natural products (+)-8, (+)-12 and (+)-15 were prepared stereoselectively for the first time, thus allowing the unambiguous assignment of their absolute configuration. (literal)

Prodotto di

• Istituto di chimica del riconoscimento molecolare (ICRM) (Istituto)
• Catalizzatori per l'abbattimento di inquinanti atmosferici (PM.P03.003.001) (Modulo)

Autore CNR

• ALESSANDRA AZZURRA COMINETTI (Persona)
• STEFANO SERRA (Unità di personale interno)

Insieme di parole chiave

• Parole chiave di "Use of (S)-trans-gamma-Monocyclofarnesol as a Useful Chiral Building Block for the Stereoselective Synthesis of Diterpenic Natural Products" (Insieme di parole chiave)

Incoming links:

Autore CNR di

• STEFANO SERRA (Unità di personale interno)
• ALESSANDRA AZZURRA COMINETTI (Persona)

Prodotto

• Istituto di chimica del riconoscimento molecolare (ICRM) (Istituto)
• Catalizzatori per l'abbattimento di inquinanti atmosferici (PM.P03.003.001) (Modulo)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi

• Natural product communications (Rivista)

Insieme di parole chiave di

• Parole chiave di "Use of (S)-trans-gamma-Monocyclofarnesol as a Useful Chiral Building Block for the Stereoselective Synthesis of Diterpenic Natural Products" (Insieme di parole chiave)