Synthetic process for fk-506 type macrolide intermediates

Details Synthetic process for fk-506 type macrolide intermediates Synthetic process for fk-506 type macrolide intermediates

C - Chemistry, Metallurgy

07

F

260/325.1, 260/4

C07F 7/08 (2006.01) C07D 207/16 (2006.01) C07D 211/60 (2006.01) C07D 413/12 (2006.01) C07D 498/08 (2006.01) C07D 498/18 (2006.01) C07F 7/18 (2006.01)

Patent

CA 2020072

7478P/ 6/27/89:Fl 17931 TITLE OF THE INVENTION NEW SYNTHETIC PROCESS FOR FK-506 TYPE MACROLIDE INTERMEDIATES ABSTRACT OF THE DISCLOSURE A process for the conversion of FR-506 (I,R = allyl;1) to FK-525 (XV) and analogous 23-membered ring macrolides differing in the C.1-N.7 segment of the molecule (e.g. XVI) and is also applicable to the analogs FK-523 (XVII) and FK-520 (XVIII). The overall process consists of three stages: (a) initial degradation of the primary macrolide to an acyclic fragment containing a selectively protected C.10-C.34 framework with a protected aldehyde function at C.10 and a free hydroxyl function at C.26, (b) reacylation of the C.26 hydroxyl function with an appropriately N-protected alpha-amino acid moiety, and (c) reintroduction of the C.8 and C.9 carbons followed by regeneration of the FK-macrolide system.

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