Literature DB >> 29498864

Schinortriterpenoids with Identical Configuration but Distinct ECD Spectra Generated by Nondegenerate Exciton Coupling.

Yi-Ming Shi1, Kun Hu1,2, Gennaro Pescitelli3, Miao Liu1, Xiao-Nian Li1, Xue Du1, Wei-Lie Xiao1, Han-Dong Sun1, Pema-Tenzin Puno1.   

Abstract

Ten schinortriterpenoids with biogenetically related lancischiartane scaffolds, including the first 3-norlancischiartane (1) with unusual configuration inversions occurring at C-1 and C-10, were isolated from Schisandra lancifolia. Unusual ECD curve patterns observed in 6-8 were confirmed to be caused by nondegenerate exciton coupling, suggesting that ECD spectrum empirical comparison should be used with caution in configuration determination. Additionally, structure revision of 2, originally proposed as arisanlactone A, was completed using NMR computation and X-ray diffraction analysis.

Entities:  

Year:  2018        PMID: 29498864     DOI: 10.1021/acs.orglett.8b00149

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  2 in total

Review 1.  ECD exciton chirality method today: a modern tool for determining absolute configurations.

Authors:  Gennaro Pescitelli
Journal:  Chirality       Date:  2021-11-17       Impact factor: 2.183

Review 2.  Harvest, After 50 Years of Sowing.

Authors:  Pema-Tenzin Puno
Journal:  Nat Prod Bioprospect       Date:  2018-07-19
  2 in total

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