American Chemical Society
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Total Synthesis and Proof of Structure of a Human Breast Tumor (Globo-H) Antigen

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journal contribution
posted on 1996-11-20, 00:00 authored by Tae Kyo Park, In Jong Kim, Shuanghua Hu, Mark T. Bilodeau, John T. Randolph, Ohyun Kwon, Samuel J. Danishefsky
The total synthesis of the Hakomori MBr1 antigen, heavily expressed on human breast tumors, is related. The construction involved the assembly of four glycals:  (17 (twice), 18, 20, and 26) and an l-fucose derivative, 34. The sensitivity of the stereochemistry of sulfonamido galactosylation by a terminal galactose ring as a function of the state of protection status of its C4 alcohol was exploited in a key step. (See the formation of compound 51.) The synthesis served to confirm the Hakomori assignment of structure, and paves the way for immunoconjugation. (See compound 64.)