File:Sherburn's Total Synthesis of (-)-Artigenin.png

Sherburn's Total Synthesis of (-)-Arctigenin

The following synthesis begins at the top left and follows the respective arrows to the bottom left product, (-)-Arctigenin.

[1]The first step involves the formation of the boron enolate of the oxazolidinone (right structure), which then is reacted with the given aldehyde(left) to produce this first structure in an approximate 92% yield.

[2]In the following two steps the chiral alcohol is protected by the creation of an -OTBS group (down left). After which the oxazolidinone is removes to form a terminal alcohol (far right).

[3]The para protected alcohol aldehyde (left), is reduced to an alcohol (center), the alcohol is reacted with thiophosgene (CSCl2) to produce a very reactive C-Cl bond.

[4]The terminal alcohol from structure [2] reacts with the C-Cl bond from structure [3] to produce a combined product (far right)[5]

[5](add link to radical rxn here)

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