عنوان

Some uses of nuclear magnetic resonance spectroscopy in the structure elucidation of isoquinoline alkaloids

Number

TLpq303712853

.Language of Text, Soundtrack etc

انگلیسی

Title Proper

Some uses of nuclear magnetic resonance spectroscopy in the structure elucidation of isoquinoline alkaloids

General Material Designation

[Thesis]

First Statement of Responsibility

A. J. Freyer

Subsequent Statement of Responsibility

M. Shamma

Name of Publisher, Distributor, etc.

The Pennsylvania State University

Date of Publication, Distribution, etc.

1988

Specific Material Designation and Extent of Item

93

Dissertation or thesis details and type of degree

Ph.D.

Body granting the degree

The Pennsylvania State University

Text preceding or following the note

1988

Text of Note

Roemeria refracta of Turkish origin had formerly provided a number of alkaloids suspected of belonging to the pavine-isopavine grouping. As a result of the present effort, it was demonstrated that one of these bases, ()-eschscholtzinone, is the first ketonic pavinoid. ()-Norreframidine is the only naturally occurring N-norisopavine. The new isopavine ()-refractamine, structurally isomeric with the known ()-reframoline, was also characterized. The different di, tetra and hexahydro derivatives of the proaporphine (+)-stepharine, which had previously been obtained through catalytic reduction, were studied by various NMR techniques, thus allowing for specific stereochemical assignments. A number of Roemeria proaporphines alkaloids wre subjected to NMR analyses and their structures elucidated. ()-Roemerialinone, ()-isoorientalinone, ()-isoroemerialinone, ()-11,12-dihydroorientalinone, (+)-8,9-dihydroisoroemerialinone and ()-usd\alphausd-roemehybrine were thus identified. Two previously known alkaloids from R. hybrida, namely ()-roehybridine and ()-roemeridine, were shown to belong to the new class of isoquinoline-indole bases formed by Pictet-Spengler condensation of a ketonic tetrahydroproaporphine with a tryptamine analog. Finally, the NMR spectral characteristics of over 100 bisbenzylisoquinoline alkaloids have been presented in tabular form. The use of this extensive data in the structure elucidation of new bisbenzylisoquinolines has been demonstrated.

NMR

Nuclear chemistry

Pure sciences

A. J. Freyer

M. Shamma

Electronic name

p

[Thesis]

276903

a

Y