Total solid phase syntheses of the quinazoline alkaloids: Verrucines A and B and anacine

Journal of Natural Products

Volumn 64, Issue 12, 2001, Pages 1497-1501

  Wang, Haishan ^a   Sim, Mui Mui ^a  

^a INSTITUTE OF MOLECULAR AND CELL BIOLOGY   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

1 HYDROXYVERRUCINE B; ALKALOID; ANACINE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG; VERRUCINE A; VERRUCINE B;

ARTICLE; CHEMICAL REACTION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; STEREOSPECIFICITY; STRUCTURE ANALYSIS;

ACYLATION; ALKALOIDS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PENICILLIUM; QUINAZOLINES; RESINS, PLANT; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM;

EID: 0035681035     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np010342y     Document Type: Article

References (20)

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18. Epimerization may be due to the strongly acidic condition. Numata et al. (ref 3) pointed out that the fumiquinazolines epimerized at both C-1 and C-4 positions under strongly basic conditions, but epimerized at C-1 only under strongly acidic conditions. C-6 - benzene ring - N-11-C-11a-C-1 is a highly conjugated unsaturated ketone-like system. The interchangeable ketone and enol forms are the driving force for epimerization at the C-1 position. (Equation Presented)
19. Optical rotation data of anacine and its natural diastereoisomer were not reported in the original paper (ref 6). The value reported here was obtained from the authentic sample provided by Professor Mantle.
20. The authentic samples of verrucines A and B were not available.