Isolation and structure elucidation of two new alkaloids, pandamarilactonine-C and -D, from Pandanus amaryllifolius and revision of relative stereochemistry of pandamarilactonine-A and -B by total synthesis

Chemical and Pharmaceutical Bulletin

Volumn 50, Issue 9, 2002, Pages 1303-1304

  Takayama, Hiromitsu ^a   Ichikawa, Tomotake ^a   Kitajima, Mariko ^a   Nonato, Maribel G ^b   Aimi, Norio ^a  

^a CHIBA UNIVERSITY   (Japan)

^b UNIVERSITY OF SANTO TOMAS   (Philippines)

Author keywords

Pandamarilactonine; Pandanus; Pyrrolidine alkaloid; Structure elucidation; Structure revision; Total synthesis

Indexed keywords

ALKALOID DERIVATIVE; PANDAMARILACTONINE A; PANDAMARILACTONINE B; PANDAMARILACTONINE C; PANDAMARILACTONINE D; PANDANUS AMARYLLIFOLIUS EXTRACT; PLANT EXTRACT; UNCLASSIFIED DRUG; ALKALOID; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; METHYL 2 (BIS(2,2,2 TRIFLUOROETHYL)PHOSPHONO)PROPIONATE; METHYL 2-(BIS(2,2,2-TRIFLUOROETHYL)PHOSPHONO)PROPIONATE; ORGANOPHOSPHORUS COMPOUND; PANDAMARILACTONINE-C; PANDAMARILACTONINE-D; PROPIONIC ACID DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; MANNICH REACTION; MASS SPECTROMETRY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY ANALYSIS; CHEMISTRY; CONFORMATION; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PANDANACEAE; PHILIPPINES; STEREOISOMERISM; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

ALKALOIDS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; ORGANOPHOSPHORUS COMPOUNDS; PANDANACEAE; PHILIPPINES; PROPIONATES; PYRROLIDINES; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM;

EID: 0036725804     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.50.1303     Document Type: Article

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8. 3) δ: 174.2 (C-18), 171.0 (C-2), 148.7 (C-5), 146.7 (C-16), 131.3 (C-17), 130.3 (C-4), 129.1 (C-3), 113.4 (C-6), 83.8 (C-15), 65.6 (C-14), 55.2 (C-9), 54.2 (C-11), 29.1 (C-8), 26.1 (C-12), 24.2 (C-7), 23.8 (C-13), 10.8 (C-20, C-21).
9. 3) δ: 174.3 (C-18), 171.0 (C-2), 149.0 (C-5), 147.1 (C-16), 131.0 (C-17), 133.9 (C-4), 130.3 (C-3), 113.3 (C-6), 83.0 (C-15), 65.9 (C-14), 55.1 (C-9), 54.0 (C-11), 28.7 (C-8), 26.3 (C-12), 24.0 (C-7), 23.9 (C-13), 10.8 (C-20), 10.7 (C-21).
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12. Note added in proof: After submission of the paper, a total synthesis of pandamarilactonine-A and -B was published, Busque F., March P., Figueredo M., Font J., Sanfeliu E., Tetrahedron Lett., 43, 5583-5585 (2002).