125736-07-4

Upstream product

• 186581-53-3 diazomethane 
• 125736-05-2 (1R,2R,6R)-9-Aza-bicyclo[4.2.1]nonane-2,9-dicarboxylic acid 9-tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 31598-70-6 cis-cyclooct-4-enone 
• 125736-01-8 (1R,2R,6R)-2-[1-(tert-Butyl-dimethyl-silanyloxy)-vinyl]-9-aza-bicyclo[4.2.1]nonane-9-carboxylic acid tert-butyl ester 
• 125736-04-1 C₂₀H₃₇NO₄Si 
• 129001-05-4 C₁₇H₂₇NO₄S₂ 
• 112020-12-9 trans-N-Boc-dihydroanatoxin-a 
• 147330-13-0 methyl N-(4-cyclooctenyl)carbamate 
• 70423-71-1 (Z)-cyclooct-4-en-1-amine 
• 68344-35-4 cyclooct-4-enone oxime 

Downstream Products

• 125736-37-0 2-Bromo-9-aza-bicyclo[4.2.1]nonane-2,9-dicarboxylic acid 9-tert-butyl ester 2-methyl ester 
• 125736-10-9 9-Aza-bicyclo[4.2.1]non-2-ene-2,9-dicarboxylic acid 9-tert-butyl ester 2-methyl ester 
• 90741-49-4 (R)-2-Acetyl-9-aza-bicyclo[4.2.1]nonane-9-carboxylic acid tert-butyl ester 
• 129001-06-5 (R)-2-Chlorocarbonyl-9-aza-bicyclo[4.2.1]nonane-9-carboxylic acid tert-butyl ester 
• 125736-03-0 (R)-9-Aza-bicyclo[4.2.1]nonane-2,9-dicarboxylic acid 9-tert-butyl ester 
• 125736-08-5 2-Phenylselanyl-9-aza-bicyclo[4.2.1]nonane-2,9-dicarboxylic acid 9-tert-butyl ester 2-methyl ester 

Relevant academic research and scientific papers

A formal total synthesis of (±)-anatoxin-a by an intramolecular Pd- catalyzed aminocarbonylation reaction

9-Azabicyclo[4.2.1]nonane skeleton 3a was prepared by intramolecular aminocarbonylation of 2a catalyzed by palladium. In three steps 3a was transformed into 8 which had previously been transformed into anatoxin-a, thus completing the formal total synthesis.

Chirospecific Syntheses of Nitrogen and Side-Chain Modified Anatoxin Analogues. Synthesis of (1R)-Anatoxinal and (1R)-Anatoxinic Acid Derivatives

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.

Enantiodivergent Synthesis of (+)- and (-)-Anatoxin from L-Glutamic acid

The optically pure 2,5-difunctionalized homotropane 11, prepared from L-glutamic acid, serves as the common, advanced intermediate for the synthesis of either natural (+)-anatoxin (30, 18percent overall yield) or unnatural (-)-anatoxin (33, 30percent overall yield) by selective manipulation of either the C-2 ester or C-5 acetyl functionalities.Side-chain substitution in the decarbonylative iminium ion cyclization of a substituted proline enhanced the yield by 25percent as compared to the unsubstituted parent system.The additional substitution at C-5 of the 9-azabicyclononane ring system allows access to analogues of anatoxin not availalble through other syntheses.