Synthesis of stereospecifically deuterated desoxypodophyllotoxins and 1H-nmr assignment of desoxypodophyllotoxin

A J Pullockaran; D G Kingston; N G Lewis

doi:10.1021/np50066a015

Synthesis of stereospecifically deuterated desoxypodophyllotoxins and 1H-nmr assignment of desoxypodophyllotoxin

J Nat Prod. 1989 Nov-Dec;52(6):1290-5. doi: 10.1021/np50066a015.

Authors

A J Pullockaran¹, D G Kingston, N G Lewis

Collaborator

N G Lewis²

Affiliations

¹ Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg 24061-0212.
² VPI, Blacksburg, VA, Dept of Wood Science and Forest Products and Biochemistry

PMID: 11536618
DOI: 10.1021/np50066a015

Abstract

[4 beta- 2H1]Desoxypodophyllotoxin [3], [4 alpha- 2H1]desoxypodophyllotoxin [4], and [4, 4- 2 H2]desoxypodophyllotoxin [9] were prepared from podophyllotoxin [1] via its chloride [5]. A complete assignment of the 1H-nmr spectrum of desoxypodophyllotoxin [2] was made on the basis of the spectra of the deuterated compounds [3] and [4].

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Antineoplastic Agents, Phytogenic / analysis
Antineoplastic Agents, Phytogenic / biosynthesis
Deuterium / analysis
Hydrogen / analysis
Hydroxylation
Magnetic Resonance Spectroscopy*
Plant Roots / chemistry
Plant Roots / metabolism
Plants, Medicinal*
Plants, Toxic*
Podophyllotoxin / analogs & derivatives*
Podophyllotoxin / analysis
Podophyllotoxin / biosynthesis*
Podophyllum / chemistry
Podophyllum / metabolism*
Stereoisomerism

Substances

Antineoplastic Agents, Phytogenic
Hydrogen
Deuterium
Podophyllotoxin