Structural reassignment of the dehydration product of 2′-Hydroxywarfarin

1977 ◽  
Vol 14 (2) ◽  
pp. 319-320 ◽  
Author(s):  
William H. Porter ◽  
William F. Trager
Keyword(s):  
1965 ◽  
Vol 43 (7) ◽  
pp. 2012-2016 ◽  
Author(s):  
Kju Hi Shin ◽  
L. Fonzes ◽  
Léo Marion

Previous work by many authors has led to the assumption that retamine might be (+)-12-hydroxysparteine. A partial synthesis of the enantiomorph of this compound has been effected by dehydration of (+)-13-hydroxylupanine and hydroboration of the product. The dehydration product consisted of two components that were separated by thin-layer chromatography and identified by the characteristics of their nuclear magnetic resonance (n.m.r.) spectra as Δ12,13-and Δ13,14-dehydrolupanine. Hydroboration of the Δ12,13-isomer gave rise to (−)-12-hydroxy-sparteine having, in thin-layer chromatography, the same Rf value as natural retamine and the same optical rotation numerically, although of opposite sign. The synthetic base had the same infrared and n.m.r. spectra as the alkaloid and the two had superimposable Debye–Scherrer patterns. Evidence is given showing the hydroxyl to be equatorial.


Island Arc ◽  
2020 ◽  
Vol 30 (1) ◽  
Author(s):  
Tadao Nishiyama ◽  
Hibiki Eguchi ◽  
Dai Shiosaki ◽  
Akira Yoshiasa ◽  
Nobutatsu Mochizuki ◽  
...  

1972 ◽  
Vol 25 (2) ◽  
pp. 393 ◽  
Author(s):  
JT Baker ◽  
JD Blake ◽  
JK Macleod ◽  
DA Ironside ◽  
IC Johnson

Using combined gas chromatography and mass spectrometry, ten components of the scent-gland complex of the coreoid Amblypelta nitida Stal have been identified. Of specific interest is the presence in the gland reservoir of 2-n-butyloct-2-enal, the aldol condensation-dehydration product of hexanal.


ChemInform ◽  
2005 ◽  
Vol 36 (39) ◽  
Author(s):  
Shu-Wei Yang ◽  
Tze-Ming Chan ◽  
Joseph Terracciano ◽  
Reena Patel ◽  
David Loebenberg ◽  
...  
Keyword(s):  

1973 ◽  
Vol 4 (43) ◽  
pp. no-no
Author(s):  
J. AMOS ◽  
G. H. COOPER
Keyword(s):  

2019 ◽  
Vol 58 (11) ◽  
pp. 7310-7323 ◽  
Author(s):  
Marie C. Kirkegaard ◽  
J. L. Niedziela ◽  
Andrew Miskowiec ◽  
Ashley E. Shields ◽  
Brian B. Anderson

1970 ◽  
Vol 23 (11) ◽  
pp. 2325 ◽  
Author(s):  
RA Kent ◽  
IR Smith ◽  
MD Sutherland

Acetone extraction of the flesh of the comatulid crinoid Comantheria perplexa (H. L. Clark) yields a mixture of substances from which the sodium salt of the sulphuric ester (12) of 8-hydroxy-5,6-dimethoxy-2-methyl-4H-naphtho[2,3-b]pyran-4-one (8) has been isolated. Acid hydrolysis of (12) yields the phenol (8) which on methylation is converted into rubrofusarin dimethyl ether and on partial demethylation yields a product identical with a dehydration product (10) of fonsecin. Hydrolysis of the crude extract from C. perplexa yields (8), (10), and 8-hydroxy-5,6-dimethoxy-2-n-propyl-4H-naphtho[2,3-b]pyran-4-one (13). The structures of the isolated substances suggest a polyketide-type synthetic activity by this species. The stalked crinoids Endoxocrinus parrae (Gervais) and Neocrinus decorus (Wyville Thomson) yield negligible quantities of aromatic polyketides.


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