Structural revisions of some non-adjacent bis-tetrahydrofuran annonaceous acetogenins.
The relative stereochemistries of bullatalicin [1] and bullatalicinone [2] were partially reassigned based on COSY and relayed COSY spectra. The structures of annonins VIII [3], IV [4], and XVI [5] were revised and concluded as bullatalicin [1], bullatanocin [6], and squamostatin A [7], respectively.
Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907.
X P
XP
Fang
Z M
ZM
Gu
M J
MJ
Rieser
Y H
YH
Hui
J L
JL
McLaughlin
M
M
Nonfon
F
F
Lieb
H F
HF
Moeschler
D
D
Wendisch
D000230:Adenocarcinoma / Q000188:drug therapy; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000494:pharmacology; D001943:Breast Neoplasms / Q000188:drug therapy; D002277:Carcinoma / Q000188:drug therapy; D003110:Colonic Neoplasms / Q000188:drug therapy; D005663:Furans / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D010946:Plants, Medicinal / Q000737:chemistry*; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; C083157:bullatalicin; C083156:bullatalicinone