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Pls provide arrows for mechanism, I will rate. thank you 1. Lycopodine is a naturally occurring amine. As such, it belongs to the family of

Pls provide arrows for mechanism, I will rate. thank you

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1. Lycopodine is a naturally occurring amine. As such, it belongs to the family of natural products called alkaloids. Its synthesis (). Am. Chem. Soc. 1968, 90, 1647-1648) was accomplished by one of the great synthetic organic chemists of our time, Gilbert Stork (Columbia University). Write a detailed mechanism for all the steps that occur when 2 reacts with ethyl acetoacetate in the presence of ethoxide ion. Note that a necessary part of the mechanism will be a haso-catalyzed isomerization (via a conjugated enclate) of the alkene in 2 to form the corresponding 0.3-unsaturated ester Me H H Me H o CH OMe H .CO.Et (1) NOEL, OH (2) HO 3) HO. ETO, 2 OH Me Lycopodine 3

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