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

1989-06-30

1992-11-17

Shaver, Paul F.

Organic compounds -- part of the class 532-570 series

Organic compounds

Silicon containing

556445, 568670, 568630, C07F 708, C07F 718

Patent

active

051645254

ABSTRACT:
A process for the conversion of FK-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.

REFERENCES:
patent: 5011943 (1991-04-01), Wang
J. Am. Chem. Soc., 109, 5031 (1987).
J. Am. Chem. Soc., 111, 1157 (1989).

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