Ring strain causes planar chirality in tedarene A and B, two cyclic diarylheptanoids isolated from the marine sponge Tedania ignis. In both molecules, the chiral plane is an olefinic system, which is very rare among natural products. In tedarene A (1) interconversion is too fast to allow isolation of the enantiomeric atropisomers, but still slow enough to cause coalescence of some 1H and 13C NMR signals at room temperature. In tedarene B (2), which also shows stable central and axial chirality, the two planar diastereomers are in slow equilibrium. Tedarene B is the smallest natural product with central, axial, and planar chirality in the same simple molecule. The identification of planar chirality as the difference between its conformational isomers allowed the use of theoretical prediction of the CD spectrum to determine the absolute configuration of the stereogenic carbon C-9 as well as of the biphenyl chiral axis.

Tedarenes A and B: Structural and Stereochemical Analysis of Two New Strained Cyclic Diarylheptanoids from the Marine SpongeTedania ignis / Costantino, Valeria; Fattorusso, Ernesto; Mangoni, Alfonso; Perinu, Cristina; Teta, Roberta; Panza, Elisabetta; Ianaro, Angela. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 77:15(2012), pp. 6377-6383. [10.1021/jo300295j]

Tedarenes A and B: Structural and Stereochemical Analysis of Two New Strained Cyclic Diarylheptanoids from the Marine SpongeTedania ignis

COSTANTINO, VALERIA;FATTORUSSO, ERNESTO;MANGONI, ALFONSO
;
PERINU, CRISTINA;TETA, ROBERTA;PANZA, ELISABETTA;IANARO, ANGELA
2012

Abstract

Ring strain causes planar chirality in tedarene A and B, two cyclic diarylheptanoids isolated from the marine sponge Tedania ignis. In both molecules, the chiral plane is an olefinic system, which is very rare among natural products. In tedarene A (1) interconversion is too fast to allow isolation of the enantiomeric atropisomers, but still slow enough to cause coalescence of some 1H and 13C NMR signals at room temperature. In tedarene B (2), which also shows stable central and axial chirality, the two planar diastereomers are in slow equilibrium. Tedarene B is the smallest natural product with central, axial, and planar chirality in the same simple molecule. The identification of planar chirality as the difference between its conformational isomers allowed the use of theoretical prediction of the CD spectrum to determine the absolute configuration of the stereogenic carbon C-9 as well as of the biphenyl chiral axis.
2012
Tedarenes A and B: Structural and Stereochemical Analysis of Two New Strained Cyclic Diarylheptanoids from the Marine SpongeTedania ignis / Costantino, Valeria; Fattorusso, Ernesto; Mangoni, Alfonso; Perinu, Cristina; Teta, Roberta; Panza, Elisabetta; Ianaro, Angela. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 77:15(2012), pp. 6377-6383. [10.1021/jo300295j]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/457605
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