Abstract
Exposure of epipodophyllotoxin C4-sulfoxides to triflic anhydride, followed by a silyl glycoside, provides a glycoconjugate of the etoposide variety via formal "reverse Kahne glycosylation." To our knowledge, this is the first example of this variant of the Kahne activation method wherein the activating functionality is positioned on the aglycon, rather than on the sugar. Phenols, anilines, or allyl silanes are also efficiently captured at C4, producing the corresponding O-, N-, and C-linked lignan conjugates.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 1149-1152 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 2 |
| Issue number | 8 |
| DOIs | |
| State | Published - Apr 20 2000 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Berkowitz, D. B., Choi, S., Bhuniya, D., & Shoemaker, R. K. (2000). Novel "reverse Kahne-type glycosylation": Access to O-, N-, and C-linked epipodophyllotoxin conjugates. Organic Letters, 2(8), 1149-1152. https://doi.org/10.1021/ol005732a