By Michael Smith
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6. Brefeldin A (161). 43 Development of the acyclic residue (C,,-C,,> began with the HBr cleavage of a-acetyl-y-butyrolactone (162) and reduction of the intermediate ketone to bromoalcohol 163 in 85% yield. Protection of the alcohol and displacement of the halogen with acetylide ion then gave a 98% yield of 164. Syn addition of tributyltin hydride proceeded in 94% yield via a radical chain mechanism to give olefin 165, whose 2-geometry is to become the A10711 double bond. Metalation and formation of the cuprate 166 then set the stage for construction of the cyclopentane ring.
Base treatment then afforded an 87% yield of cyclopentanes 205 epimeric at the nitrile (an epimerizable position). Hydrolysis and esterification of either isomer led to the trans geminally substituted cyclopentane 206 in 82% yield. Reduction of 206 and protection of the ester produced benzyl ether 207,which was converted to alkyne 208 via a bromination-dehydrobromination sequence in 78% yield. The acyclic segment required for this approach was derived from L-glutamic acid, which was readily converted to lactone 209 along conventional lines.
Clearly the utilization of a furfural moiety as a hydroxy 1,4 dicarbonyl equivalent was the linchpin of this as well as several other syntheses in this area. 56a D-Glucose was converted via previously published procedures to the protected hexose 9. Benzylation of the hydroxy groups and cleavage of the thioacetal then gave intermediate 10 in 80% yield. This fragment will later be annealed onto a carbon chain and become C-1 to C-6 of the natural product. A second fragment, also derived from D-glucose, which will correspond to C-13 to C-16, was constructed as follows.