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Enantiomeric Neolignans and a Sesquiterpene from Solanum erianthum and Their Absolute Configuration Assignment
Author(s) -
Li Hang,
Peng ShiYi,
Yang DePo,
Bai Bai,
Zhu LongPing,
Mu ChunYou,
Tian YiJing,
Wang DongMei,
Zhao ZhiMin
Publication year - 2016
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22571
Subject(s) - chemistry , absolute configuration , chromophore , chirality (physics) , stereochemistry , sesquiterpene , enantiomer , circular dichroism , axial chirality , conjugated system , cotton effect , vibrational circular dichroism , helicity , double bond , allylic rearrangement , photochemistry , organic chemistry , enantioselective synthesis , chiral symmetry , polymer , physics , particle physics , quantum mechanics , nambu–jona lasinio model , quark , catalysis
One pair of new C‐8–C‐3′/C‐7–O–C‐4′ linked neolignan enantiomers ( 1a / 1b ) and one new guaiane sesquiterpene ( 2 ) first featuring the 1(2),9(10)‐conjugated double bond were isolated from the stems of Solanum erianthum (Solanceae). Their structures were characterized on the basis of extensive spectroscopic analyses, especially from their 2D nuclear magnetic resonance (NMR) spectra. The absolute configurations of 1a / 1b were rigorously elucidated by electronic circular dichroism (ECD) experiments combined with the reversed helicity rule for the 2,3‐dihydrobenzo[b]furan chromophore, and compound 2 is the first report on the sterochemical assignment of a guaiane sesquiterpene by using the allylic axial chirality rule for the conjugated diene chromophore in combination with the calculated ECD spectrum. Chirality 28:259–263, 2016 . © 2016 Wiley Periodicals, Inc.