Preparation of glucosidic derivatives of steganol

Rickey P. Hicks; Albert T. Sneden

doi:10.1021/np50039a002

Preparation of glucosidic derivatives of steganol

Rickey P. Hicks, Albert T. Sneden

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

7 Scopus citations

Abstract

Glucoside derivatives of steganol (1) analogous to the semisynthetic podophyllotoxin derivative, VP 16–213, were prepared. Glucosidation of steganol (1) with 2,3,4,6-tetra-0-benzylglucopyranose gave the a-anomer (7) of the glucoside as the major product. Subsequent removal of the benzyl groups and reaction with acetaldehyde dimethyl acetal gave the ethylidene derivative 10. The β-anomer (8) of the glucoside was similarly converted to 12. All derivatives prepared were screened for activity in the DNA breakage assay.

Original language	English (US)
Pages (from-to)	357-362
Number of pages	6
Journal	Journal of Natural Products
Volume	48
Issue number	3
DOIs	https://doi.org/10.1021/np50039a002
State	Published - May 1985
Externally published	Yes

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

Access to Document

10.1021/np50039a002

Cite this

@article{97f736717df64632b1f851ff198bf6f3,

title = "Preparation of glucosidic derivatives of steganol",

abstract = "Glucoside derivatives of steganol (1) analogous to the semisynthetic podophyllotoxin derivative, VP 16–213, were prepared. Glucosidation of steganol (1) with 2,3,4,6-tetra-0-benzylglucopyranose gave the a-anomer (7) of the glucoside as the major product. Subsequent removal of the benzyl groups and reaction with acetaldehyde dimethyl acetal gave the ethylidene derivative 10. The β-anomer (8) of the glucoside was similarly converted to 12. All derivatives prepared were screened for activity in the DNA breakage assay.",

author = "Hicks, {Rickey P.} and Sneden, {Albert T.}",

year = "1985",

month = may,

doi = "10.1021/np50039a002",

language = "English (US)",

volume = "48",

pages = "357--362",

journal = "Journal of Natural Products",

issn = "0163-3864",

publisher = "American Chemical Society",

number = "3",

}

TY - JOUR

T1 - Preparation of glucosidic derivatives of steganol

AU - Hicks, Rickey P.

AU - Sneden, Albert T.

PY - 1985/5

Y1 - 1985/5

N2 - Glucoside derivatives of steganol (1) analogous to the semisynthetic podophyllotoxin derivative, VP 16–213, were prepared. Glucosidation of steganol (1) with 2,3,4,6-tetra-0-benzylglucopyranose gave the a-anomer (7) of the glucoside as the major product. Subsequent removal of the benzyl groups and reaction with acetaldehyde dimethyl acetal gave the ethylidene derivative 10. The β-anomer (8) of the glucoside was similarly converted to 12. All derivatives prepared were screened for activity in the DNA breakage assay.

AB - Glucoside derivatives of steganol (1) analogous to the semisynthetic podophyllotoxin derivative, VP 16–213, were prepared. Glucosidation of steganol (1) with 2,3,4,6-tetra-0-benzylglucopyranose gave the a-anomer (7) of the glucoside as the major product. Subsequent removal of the benzyl groups and reaction with acetaldehyde dimethyl acetal gave the ethylidene derivative 10. The β-anomer (8) of the glucoside was similarly converted to 12. All derivatives prepared were screened for activity in the DNA breakage assay.

UR - http://www.scopus.com/inward/record.url?scp=0021880505&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0021880505&partnerID=8YFLogxK

U2 - 10.1021/np50039a002

DO - 10.1021/np50039a002

M3 - Article

C2 - 4031896

AN - SCOPUS:0021880505

SN - 0163-3864

VL - 48

SP - 357

EP - 362

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 3

ER -

Preparation of glucosidic derivatives of steganol

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this