Lewis acid- and Bronsted acid-catalyzed stereoselective rearrangement of epoxides derived from himachalenes: access to new chiral polycyclic structures

Haib, Abderrahim El; Benharref, Ahmed; Parrès-Maynadié, Sandra; Manoury, Éric; Urrutigoı̈ty, Martine; Gouygou, Maryse

doi:10.1016/j.tetasy.2010.12.013

Cited by 46 publications

(29 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The reactivity of these sesquiterpenes and their derivatives have been studied extensively by our team in order to prepare new products having biological proprieties (El Haib et al, 2011;Benharref et al, 2013Benharref et al, , 2015Benharref et al, , 2016Zaki et al, 2014). Indeed, these compounds have been tested, using the food poisoning technique, for their potential antifungal activity against the phytopathogen Botrytis cinerea (Daoubi et al, 2004).…”

Section: Structure Descriptionmentioning

confidence: 99%

1-(7-Isopropyl-2,5-dimethyl-8-nitronaphthalen-1-yl)ethanone

et al. 2017

Self Cite

View full text Add to dashboard Cite

The title compound, C17H19NO3, was synthesized in three steps from a mixture of α-, β- and γ-himachalene, which was isolated from an essential oil of the Atlas cedar (Cedrus atlantica). The dihedral angle between the two rings of the naphthalene moiety is 2.54 (5)°. The nitro group and the acetyl group lie almost normal to the mean plane of the naphthalene moiety, making dihedral angles of 80.29 (13) and 83.01 (15)°, respectively, and are inclined to one another by 13.23 (19)°. There is an intramolecular C—H...O hydrogen bond present involving a nitro O atom and the H atom of the methine C atom of the isopropyl group, forming anS(6) ring motif. In the crystal, molecules are linked by pairs of C—H...π interactions, forming inversion dimers. There are no other significant intermolecular interactions present.

show abstract

Section: Structure Descriptionmentioning

confidence: 99%

1-(7-Isopropyl-2,5-dimethyl-8-nitronaphthalen-1-yl)ethanone

et al. 2017

Self Cite

View full text Add to dashboard Cite

show abstract

“…The bicyclic sesquiterpene -himachalene is the main constituent of the essential oil of the Atlas cedar (Cedrus atlantica) (El Haib et al, 2011). The reactivity of this sesquiterpene (and its derivatives) has been studied extensively by our team in order to prepare new products having biological properties (El Jamili et al, 2002;Benharref et al, 2013Benharref et al, , 2015Benharref et al, , 2016Zaki et al, 2014).…”

Section: Structure Descriptionmentioning

confidence: 99%

1-[(1R,2S,4R,7S)-3,3-Dichloro-4,11,11-trimethyltricyclo[5.4.0.0^2,4]undecan-7-yl]ethanone

et al. 2017

Self Cite

View full text Add to dashboard Cite

The title compound, C16H24Cl2O, crystallizes with two independent molecules in the asymmetric unit. Each molecule is built up from two fused six-membered rings, one of which is fused to a three-membered ring. The two molecules differ essentially in the orientation of two of the methyl groups. The dihedral angles between the mean planes through the two six-membered rings are 57.98 (13) and 55.29 (13)°. The molecular conformation is stabilized by intramolecular C—H...Cl hydrogen bonds.

show abstract

“…The reactivity of this sesquiterpene and its derivatives has been studied extensively by our team (El Jamili et al, 2002;El Haib et al, 2011;Loubidi et al, 2014;Benharref et al, 2016Benharref et al, , 2017 in order to prepare new products with biological properties. Indeed, these compounds have been tested, using the food-poisoning technique, for their potential antifungal activity against the phytopathogen Botrytis cinerea (Daoubi et al, 2004).…”

Section: Structure Descriptionmentioning

confidence: 99%

N-[1,4,4-Trimethyltricyclo[6.3.1.0^3,9]dodec-8(12)-en-2-yl]acetamide

et al. 2017

Self Cite

View full text Add to dashboard Cite

The title compound, C17H27NO, crystallizes with three independent molecules in the asymmetric unit with almost identical conformations. Each molecule is built up from a seven-membered ring to which a bridged six-membered ring is fused. In each of the three molecules, the seven-membered rings have a twist-chair conformation, while the cyclohexenyl rings display perfect boat conformations. In the crystal, N—H...O hydrogen bonds link the molecules into zigzag chains running along theb-axis direction.

show abstract

Lewis acid- and Bronsted acid-catalyzed stereoselective rearrangement of epoxides derived from himachalenes: access to new chiral polycyclic structures

Cited by 46 publications

References 47 publications

1-(7-Isopropyl-2,5-dimethyl-8-nitronaphthalen-1-yl)ethanone

1-(7-Isopropyl-2,5-dimethyl-8-nitronaphthalen-1-yl)ethanone

1-[(1R,2S,4R,7S)-3,3-Dichloro-4,11,11-trimethyltricyclo[5.4.0.0^2,4]undecan-7-yl]ethanone

N-[1,4,4-Trimethyltricyclo[6.3.1.0^3,9]dodec-8(12)-en-2-yl]acetamide

Contact Info

Product

Resources

About

Lewis acid- and Bronsted acid-catalyzed stereoselective rearrangement of epoxides derived from himachalenes: access to new chiral polycyclic structures

Cited by 46 publications

References 47 publications

1-(7-Isopropyl-2,5-dimethyl-8-nitronaphthalen-1-yl)ethanone

1-(7-Isopropyl-2,5-dimethyl-8-nitronaphthalen-1-yl)ethanone

1-[(1R,2S,4R,7S)-3,3-Dichloro-4,11,11-trimethyltricyclo[5.4.0.02,4]undecan-7-yl]ethanone

N-[1,4,4-Trimethyltricyclo[6.3.1.03,9]dodec-8(12)-en-2-yl]acetamide

Contact Info

Product

Resources

About

1-[(1R,2S,4R,7S)-3,3-Dichloro-4,11,11-trimethyltricyclo[5.4.0.0^2,4]undecan-7-yl]ethanone

N-[1,4,4-Trimethyltricyclo[6.3.1.0^3,9]dodec-8(12)-en-2-yl]acetamide