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Optical Resolution and Structure Determination of New Indolizidine Alkaloids from Elaeocarpus sphaericus
Author(s) -
Zhou ChangXin,
Wang XueYao,
Mo JianXia,
Zhang Jian,
Gan LiShe
Publication year - 2011
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201000200
Subject(s) - indolizidine , chemistry , circular dichroism , enantiomer , quantum chemical , resolution (logic) , absolute configuration , stereochemistry , computational chemistry , organic chemistry , alkaloid , molecule , artificial intelligence , computer science
Two new indolizidine alkaloids, (±)‐3‐oxoisoelaeocarpine ( 1 ) and (±)‐elaeocarpine N ‐oxide ( 2 ), along with three known alkaloids, (±)‐isoelaeocarpine ( 3 ), (±)‐elaeocarpine ( 4 ), and (−)‐isoelaeocarpiline ( 5 ), were isolated from an EtOH extract of the branches and leaves of Elaeocarpus sphaericus. The structures of these compounds were determined by spectroscopic and chemical methods. Furthermore, enantiomers of compounds 1 and 3 were separated on a chiral CD‐Ph column, and their absolute configurations were determined by TD‐DFT (=time‐dependent density‐functional theory) quantum‐chemical calculations of their electronic circular dichroism (ECD) spectra.