The preparation of pimecrolimus, a synthetic derivative of ascomycin endowed with immunomodulatory activity, requires the selective protection of 24-hydroxy group of the ascomycin, before elaboration of the 32 one. The aim was achieved by means of two regioselective Candida antarctica lipase-catalyzed steps. The structure of the new key intermediates, 24-, 32-monoacetates and 24,32-diacetate, was established by means of an unambiguous NMR study.
First chemoenzymatic synthesis of immunomodulating macrolactam pimecrolimus / P. Ferraboschi, D. Colombo, M. De Mieri, P. Grisenti. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 50:30(2009 Jul 29), pp. 4384-4388. [10.1016/j.tetlet.2009.05.066]
First chemoenzymatic synthesis of immunomodulating macrolactam pimecrolimus
P. FerraboschiPrimo
;D. ColomboSecondo
;M. De MieriPenultimo
;
2009
Abstract
The preparation of pimecrolimus, a synthetic derivative of ascomycin endowed with immunomodulatory activity, requires the selective protection of 24-hydroxy group of the ascomycin, before elaboration of the 32 one. The aim was achieved by means of two regioselective Candida antarctica lipase-catalyzed steps. The structure of the new key intermediates, 24-, 32-monoacetates and 24,32-diacetate, was established by means of an unambiguous NMR study.
Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
