Pinnamine (10)

Anatoxin-a (11)

1) TBSCI. EtoN

Af-Z-pyroglutamic acid z o

1) TBSCI. EtoN

Af-Z-pyroglutamic acid



Scheme 3

parasympathetic nervous system. Thus, the toxic expression of pinnamine, similar to that of atropine, may result from excitability of the cerebrum.

Recently, an enantioselective synthesis of pinnamine (10) has been achieved (Scheme 3) [22]. The 9-aza-bicyclo[4.2.1]nonane moiety in 10 was constructed by convergence of the ^-keto ester into the silyl enol ether followed by Lewis acid treatment. Synthetic pinnamine was found to correspond uniquely to the natural compound based on a comparison of their spectral data including their CD spectra.

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