Total Synthesis of Ingramycin Albocycline

Tanner s ingramycin synthesis is based on the coupling of three segments 146, 148 and 150 by using the sulfone anions. 

The segment 146 was prepared from L-serine through the methyl ketone 145. The segments 148 and 150 were prepared from alcohols 147 and 149, both of which were derived through Sharpless epoxidation and methylation. The segment 146 was treated with the anion of 148 followed by reductive desulfurization 

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