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Revision of the Absolute Configuration of Plumericin and Isoplumericin from Plumeria rubra
Author(s) -
Elsässer Brigitta,
Krohn Karsten,
Nadeem Akhtar M.,
Flörke Ulrich,
Kouam Simeon F.,
Kuigoua Merlin Guy,
Ngadjui Bonaventure T.,
Abegaz Berhanu M.,
Antus Sándor,
Kurtán Tibor
Publication year - 2005
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200590058
Subject(s) - absolute configuration , absolute (philosophy) , chemistry , circular dichroism , spectral line , quantum chemical , stereochemistry , physics , molecule , quantum mechanics , organic chemistry , philosophy , epistemology
Abstract The absolute configurations of plumericin ( 1 ) and isoplumericin ( 2 ), isolated from Plumeria rubra , were re‐assigned based on a combination of X‐ray crystal‐structure determination and quantum‐mechanical calculations of their circular dichroism (CD) spectra. The experimental CD spectra showed an excellent match with those calculated for the (1 S ,5 R ,8 R ,9 R ,10 R ) absolute configuration (corresponding to ent ‐ 1 and ent ‐ 2 , resp.), opposite to that generally accepted and published in the literature. Since the (false) plumericin configuration has been often used to derive the absolute configuration of related iridoids by chemical correlation, their absolute configurations also have to be reconsidered.