92998-50-0Relevant articles and documents
Synthesis of (±)-anatoxin-α and analogues
Parsons, Philip J.,Camp, Nicholas P.,Edwards, Neil,Ravi Sumoreeah
, p. 309 - 315 (2000)
A new and highly efficient synthesis of the potent nicotinic acetylcholine receptor agonist, anatoxin-α and its analogues is described, which uses a β-lactam ring opening-transannular cyclisation sequence to set up the bridged bicyclic framework of the natural product. The synthesis involves a cycloaddition of chlorosulfonyl isocyanate with cyclooctadiene followed by Boc protection of the resulting β-lactam. Reaction of the β- lactam with a variety of nucleophiles, followed by selenium-mediated cyclisation and oxidation gave the skeleton of anatoxin-α bearing various sidechains. The approach offers a flexible entry to useful quantities of anatoxin-α and its analogues.
Tandem reactions of anions: A short and efficient route to ±anatoxin-a
Parsons, Philip J.,Camp, Nicholas P.,Underwood, J. Mark,Harvey, Darren M.
, p. 11637 - 11642 (2007/10/03)
A new route to anatoxin-a (1) is reported which involves an anionically induced small ring opening/ring closure/ring opening cascade. The azabicyclo [4.2.1]nonane ring system of anatoxin-α is hence formed in one synthetic operation.
The use of nitrones in the synthesis of anatoxin-a, very fast death factor
Tufariello,Meckler,Pushpananda,Senaratne
, p. 3447 - 3453 (2007/10/02)
The synthesis of anatoxin-a (1) was completed by using the cycloaddition of 1-pyrroline-1-oxide (2) onto dienol (6), a reaction which proceeded with high stereoselectivity, regioselectivity, and site selectivity. The resultant adduct (i.e. 7) was oxidized to a second nitrone (i.e. 8) which undergoes a second closure to afford cycloadduct 9a with regiospecificity. The conversion of 9a into anatoxin-a hydrochloride (1 · HCl) was both direct and efficient.
