A Simple Synthesis of Amphimedine

1991 ◽  
Vol 44 (2) ◽  
pp. 277 ◽  
Author(s):  
RH Prager ◽  
C Tsopelas ◽  
T Heisler

The marine alkaloid amphimedine has been synthesized by a short sequence of reactions commencing from the known indenopyridinedione (2). Reaction with 4-pyridyllithium, followed by hydrazoic acid treatment, gave 5-(4-pyridyl)-3,6-phenanthrolin-4(3H)-one (12) which was converted into the chlorophenanthroline. The methyl-substituted fluorosulfonate salt of this compound was specifically oxidized by alkaline ferricyanide. Conversion of the pyridone into the nitrile gave the precursor which was cyclized to amphimedine by polyphosphoric acid.

1978 ◽  
Vol 31 (7) ◽  
pp. 1561 ◽  
Author(s):  
DW Johnson ◽  
LN Mander

5,8-Dimethoxy-3,4-dihydronaphthalen-1(2H)-one was converted into diazomethyl 5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthyl ketone (10) which, when treated with trifluoroacetic acid at 0°, gave 5,8- dimethoxy-4,4a-dihydro-3,4a-ethanonaphthalen-2(3H)-one (13), but at -15° gave 8-methoxy-1,2,3,4-tetrahydro-3,4a-ethanonaphthalene- 5(4aH),10-dione (14). 6-Methoxy-3,4-dihydronaphtha-len-1(2H)-one reacted with m-chloroperoxybenzoic acid to give 4,5-dihydro-1-benzoxepin-2(3H)-one (15) which after hydrolysis, ethylation and polyphosphoric acid treatment gave 5-ethoxy-8-methoxy-3,4-dihydronaphthalen-1(2H)-one (17). This compound was transformed into 5-ethoxy-8-hydroxy-1,2,3,4-tetrahydro-2-naphthoic acid (19) and thence to the ethoxy analogue of (14).


1982 ◽  
Vol 35 (8) ◽  
pp. 1645 ◽  
Author(s):  
SI Clarke ◽  
RH Prager

Two independent syntheses of the title compound (2), an analogue of perloline, are described. 9-(3,4-Dimethoxyphenyl)fluoren-9-ol reacted with hydrazoic acid in polyphosphoric acid to give 6-(3,4-dimethoxyphenyl)phenanthridine, the N-oxide of which was photolysed to 5-(3,4-dimethoxy-phenyl)phenanthridin-6-one (8) which was reduced to the title compound directly with sodium bis(2-methoxyethoxy)aluminium hydride ('Redal'), or by reduction to 5-(3,4-dimethoxypheny1)-5,6- dihydrophenanthridine followed by oxidation with N-bromosuccinimide. The phenanthridinone (8) was also synthesized by photolysis of the nitrone of 3,4-dimethoxy-N-fluorenylideneaniline.


2009 ◽  
Vol 36 (5) ◽  
pp. 362-367 ◽  
Author(s):  
K. MAEKAWA ◽  
K. SHIMONO ◽  
M. OSHIMA ◽  
Y. YOSHIDA ◽  
B. VAN MEERBEEK ◽  
...  

Author(s):  
George F. Leeper

Polysaccharide elementary fibrils are usually fasciated into microfibrils of from one hundred to a few hundred Angstroms wide. Cellulose microfibrils when subjected to acid treatment dissociate into component elementary fibrils. For pectic acid it was observed that variations in pH could cause a change in the fasciation of the elementary fibrils.Solutions of purified pectic acid and sodium phosphotungtate were adjusted to various pH levels with NaOH or HCl and diluted to give a final concentration of 0.5 and 1% for the polysaccharide and negative stains respectively. Micrographs were made of the samples after drying on a carbon film covered grid. The average number of elementary fibrils was determined by counting the number of elementary fibrils in each fascicle intersected by lines drawn across the micrograph.


2020 ◽  
Author(s):  
M Kreuter ◽  
F Bonella ◽  
N Blank ◽  
E Siegert ◽  
J Henes ◽  
...  

Synlett ◽  
1989 ◽  
Vol 1989 (01) ◽  
pp. 30-32
Author(s):  
Thomas V. Lee ◽  
Alistair J. Leigh ◽  
Christopher B. Chapleo

2006 ◽  
Vol 37 (06) ◽  
Author(s):  
M Rauchenzauner ◽  
E Haberlandt ◽  
S Scholl-Bürgi ◽  
D Karall ◽  
E Schönherr ◽  
...  

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