Lycopene is a naturally occurring amine. As such, it belongs to the family of natural products called

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Lycopene is a naturally occurring amine. As such, it belongs to the family of natural products called alkaloids. Its synthesis (J. 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 base-catalyzed isomerization (via a conjugated enolate) of the alkene in 2 to form the corresponding α, β-unsaturated ester.

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Organic Chemistry

ISBN: 978-1118875766

12th Edition

Authors: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder

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