Macrocyclic polythiaethers have been synthesized and some of their properties have been determined. The compounds reported comprise a homologous series containing two, four, or six sulfur atoms in the macrocyclic ring. One example of a five sulfur atom macrocyclic is included. The synthetic methods allow for symmetrical or unsymmetrical bridging of the ring sulfur atoms by ethylene, tri-, tetra-, penta-, and hexamethylene bridges.
Sir:Neolignansl are a group of secondary plant metabolites structurally characterized by the presence of two arylpropanoid units. In contradistinction to the related lignans the @ position of one arylpropane moiety is linked to one of three additional positions in the other. Within the class of neolignans substances with bicyclo[ 1.2.3]0ctane, hydrobenzofuran and spiro[5.5]undecane skeleton are encountered. Guianin ( 1)2 (from Aniba guianensis Aubl.), burchellin (2)3 (from Aniba burchellii Kosterm.), and futoenone (4)4 (from Piper futokadzura Sieb.
Communications to the Editor
8α-Amino-2,6-dimethylergoline is the key intermediate for
the
synthesis of a number of ergot derivatives under clinical
development. They are structurally related to the better
known
lysergic acid and its derivative, the diethylamide (LSD).
The
use of lysergic acid or its isomer, paspalic acid, both of
which
are readily available by fermentation on an industrial scale,
as
a starting material for the synthesis of
8α-amino-2,6-dimethylergoline appears to be the obvious choice as the basic
structural elements already exist. Whereas the
transformation
of the acid function to the amino moiety proceeded under
well-established conditions, the introduction of the single
methyl
group posed a major challenge to the industrial chemist.
Various methodologies are available to solve this problem,
and
the approach that involves direct metalation and
methylation
is found to be most suitable for up-scaling to multiton
quantities.
The importance of using on-line monitoring techniques
(FT-IR) in process research and development will be exemplified
by this report.
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