The Structural revision of the anti-inflammatory marine metabolites halipeptin A (1) and B (2) along with the isolation of the new related product halipeptin C (3) are reported. In particular, the heterocyclic portion of the molecule. incorrectly assigned as an oxazetidine ring, has now been characterised as a thiazoline unit by comparison of the spectral data of the natural products (1-3) with an appropriate synthetic model (10). GIAO calculated C-13 NMR chemical shifts for oxazetidine and thiazoline model compounds provide additional support to the revised structure.

Structural Revision of Halipeptins: Synthesis of the Thiazoline Unit and Isolation of Halipeptin C / CARMELA DELLA, Monica; Randazzo, Antonio; Giuseppe, Bifulco; Paola, Cimino; Maurizio, Aquino; Irene, Izzo; FRANCESCO DE, Riccardis; LUIGI GOMEZ, Paloma. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 43:33(2002), pp. 5707-5710. [10.1016/S0040-4039(02)01209-1]

Structural Revision of Halipeptins: Synthesis of the Thiazoline Unit and Isolation of Halipeptin C

RANDAZZO, ANTONIO;PAOLA CIMINO
2002

Abstract

The Structural revision of the anti-inflammatory marine metabolites halipeptin A (1) and B (2) along with the isolation of the new related product halipeptin C (3) are reported. In particular, the heterocyclic portion of the molecule. incorrectly assigned as an oxazetidine ring, has now been characterised as a thiazoline unit by comparison of the spectral data of the natural products (1-3) with an appropriate synthetic model (10). GIAO calculated C-13 NMR chemical shifts for oxazetidine and thiazoline model compounds provide additional support to the revised structure.
2002
Structural Revision of Halipeptins: Synthesis of the Thiazoline Unit and Isolation of Halipeptin C / CARMELA DELLA, Monica; Randazzo, Antonio; Giuseppe, Bifulco; Paola, Cimino; Maurizio, Aquino; Irene, Izzo; FRANCESCO DE, Riccardis; LUIGI GOMEZ, Paloma. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 43:33(2002), pp. 5707-5710. [10.1016/S0040-4039(02)01209-1]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/205496
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