Tetrahedron Letters

First chemoenzymatic synthesis of immunomodulating macrolactam pimecrolimus

P Ferraboschi, D Colombo, M De Mieri, P Grisenti

Index: Ferraboschi, Patrizia; Colombo, Diego; De Mieri, Maria; Grisenti, Paride Tetrahedron Letters, 2009 , vol. 50, # 30 p. 4384 - 4388

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Citation Number: 7

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-hydroxy group. 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 ...