Journal of Organic Chemistry p. 2829 - 2838 (1990)
Update date:2022-08-04
Topics:
Howard, Michael H.
Sardina, F. Javier
Rapoport, Henry
A straightforward and good yielding route to side-chain analogues of the potent neurotoxin and neurotransmitter (+)-anatoxin (1) has been developed.Peroxy acid oxidation of the (silyloxy)butadiene 43 derived from readily synthesized, optically pure (1R)-t-BOC-anatoxin (42) affords silyloxy ketone 44.Fluorolysis of 44 followed by oxidative cleavage of the resultant α-hydroxy ketone 45 gives a mixture of α,β-unsaturated acid 46 and ester 41 in 57percent combined yield.Other approaches to these compounds, based on literature precedent, failed. (1R)-t-BOC-anatoxinic acid (46) then serves as educt for the synthesis of a wide variety of anatoxin derivatives with modified side-chain functionality.These analogues, designed to serve as probes of the antagonist binding site of the nicotinic acetylcholine receptor, include alcohol, aldehyde, amide, hydroxamate, and oxime ether functional groups.
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Doi:10.1248/cpb.38.1012
(1990)Doi:10.1021/ja00788a034
(1973)Doi:10.1021/ol010251s
(2002)Doi:10.1039/c39800000051
(1980)Doi:10.1021/jo00962a012
(1973)Doi:10.1021/tx0155909
(2002)