Journal of Organic Chemistry p. 5451 - 5454 (1990)
Update date:2022-08-03
Topics: Catalyst Experimental Setup Chemical Reaction synthetic intermediate Degradation Pathway
Askin, D.
Joe, Daisy
Reamer, R. A.
Volante, R. P.
Shinkai, I.
An 11-step degradation of natural FK-506 (1) to selectively protected C10-C34 synthetic intermediate 2 has been accomplished in 14percent overall yield.The key steps include; (a) lead tetracetate mediated C9-C10 bond cleavage of 24,32-bis(triisopropylsilyl)-FK-506 (3), (b) simultaneous C10 ester, C22 ketone reduction/C26 oxygen deacylation, and (c) selective bis(triethylsilylation) of the resulting triols 7a,b.The degradate 2 is ready for reacylation at the C26 hydroxyl terminus; hydrolysis of the dimethyl acetal moiety then provides an aldehyde ready for homologation at the C10 terminus.
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Doi:10.1248/cpb.38.2577
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