First chemoenzymatic synthesis of immunomodulating macrolactam pimecrolimus

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-catalyz...

Full description

Bibliographic Details
Published in:Tetrahedron Letters
Main Authors: P. Ferraboschi, D. Colombo, M. De Mieri, P. Grisenti
Format: Article in Journal/Newspaper
Language:English
Published: Elsevier 2009
Subjects:
Ascomycin
Immunomodulator
Lipase
Macrolactam
Regioselectivity
Settore BIO/10 - Biochimica
Antarc*
Antarctica
Online Access:http://hdl.handle.net/2434/66629
https://doi.org/10.1016/j.tetlet.2009.05.066
Description
Summary: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.

Similar Items