NDLI: Exciton coupling circular dichroism of an allylicN-imidazolyl group in amaranzole A, a marine natural product fromPhorbas amaranthus

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Exciton coupling circular dichroism of an allylicN-imidazolyl group in amaranzole A, a marine natural product fromPhorbas amaranthus

Content Provider	Scilit
Author	Morinaka, Brandon I. Molinski, Tadeusz F.
Copyright Year	2008
Description	Journal: Chirality A new steroidal alkaloid amaranzole A (10 ) with a C24‐imidazolyl group displays an unusually large split‐CD spectrum at short wavelengths that we assign to exciton coupled circular dichroism (ECCD) between the polarized π‐π* transitions of the C25 CC double bond and the imidazolyl group. A model 4,5‐disubstituted imidazole 11 , prepared from optically pure (R )‐(–)‐2‐aminobutanol, exhibited similar ECCD and solvent and pH‐dependence consistent with changes in the protonation state of the imidazole ring. Calculations and CD measurement of 12 (the dihydro‐derivative of 11 ) suggest that the 4‐hydroxyphenyl group is not strongly conjugated to the imidazole group in 10 , and the observed ECCD is entirely accounted for by coupling between the CC double bond and isolated imidazole π‐π* transitions. Chirality, 2008.
Related Links	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2615005/pdf
Ending Page	1070
Page Count	5
Starting Page	1066
e-ISSN	1520636X
DOI	10.1002/chir.20636
Journal	Chirality
Issue Number	9
Volume Number	20
Language	English
Publisher	Wiley-Blackwell
Publisher Date	2008-08-08
Access Restriction	Open
Subject Keyword	Journal: Chirality Organic Chemistry Circular Dichroism Natural Product Exciton Coupling
Content Type	Text
Resource Type	Article

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