Novel "reverse Kahne-type glycosylation": Access to O-, N-, and C-linked epipodophyllotoxin conjugates

David B. Berkowitz; Sungjo Choi; Debnath Bhuniya; Richard K. Shoemaker

doi:10.1021/ol005732a

Novel "reverse Kahne-type glycosylation": Access to O-, N-, and C-linked epipodophyllotoxin conjugates

David B. Berkowitz, Sungjo Choi, Debnath Bhuniya, Richard K. Shoemaker

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

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	https://doi.org/10.1021/ol005732a
State	Published - Apr 20 2000

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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T2 - Access to O-, N-, and C-linked epipodophyllotoxin conjugates

AU - Berkowitz, David B.

AU - Choi, Sungjo

AU - Bhuniya, Debnath

AU - Shoemaker, Richard K.

PY - 2000/4/20

Y1 - 2000/4/20

N2 - 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.

AB - 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.

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Novel "reverse Kahne-type glycosylation": Access to O-, N-, and C-linked epipodophyllotoxin conjugates

Abstract

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