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; Bifulco, Giuseppe; Aquino, Maurizio; Izzo, Irene; FRANCESCO DE RICCARDIS, ; LUIGI GOMEZ PALOMA, ; Cimino, Paola. - 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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
