Optical Resolution and Structure Determination of New Indolizidine Alkaloids from Elaeocarpus sphaericus

✍ Scribed by Chang-Xin Zhou; Xue-Yao Wang; Jian-Xia Mo; Jian Zhang; Li-She Gan

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: German
• Weight: 239 KB
• Volume: 94
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.201000200

✦ Synopsis

Two new indolizidine alkaloids, (AE)-3-oxoisoelaeocarpine ( 1) and (AE)-elaeocarpine N-oxide (2), along with three known alkaloids, (AE)-isoelaeocarpine (3), (AE)-elaeocarpine (4), and (À)-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 (¼ time-dependent density-functional theory) quantumchemical calculations of their electronic circular dichroism (ECD) spectra.