(1S,3R,8R,11S)-2,2,11-Tribromo-10-bromomethyl-3,7,7-trimethyltricyclo[6.4.0.01,3]dodec-9-ene

Abdoullah Bimoussa (1) , Aziz Auhmani (1) , My Youssef Ait Itto (1) , Jean-Claude Daran (2) , Abdelwahed Auhmani (1)

1 Laboratoire de Physico-Chimie Moléculaire et Synthèse Organique, Département de Chimie, Faculté des Sciences
2 LCC - Laboratoire de chimie de coordination

The title compound, C16H22Br4, was synthesized in two steps from [beta]-himachalene, which was isolated from essential oil of the Atlas cedar (cedrus atlantica). It is built up from three fused rings, a seven-membered heptane ring, a six-membered cyclohexyl ring bearing both a bromine and a bromomethyl substituent, and a three-membered propane ring bearing two Br atoms. In the crystal, molecules are linked by C-H...Br hydrogen bonds, forming chains propagating along [001]. The absolute configuration was deduced from the chemical pathway and confirmed by resonant scattering [Flack parameter = 0.012 (10)].

Mots clés: Crystal structure; Absolute configuration; Sesquiterpene; Asymmetric synthesis; Natural products

Domaines: Chimie de coordination

Abdoullah Bimoussa, Aziz Auhmani, My Youssef Ait Itto, Jean-Claude Daran, Abdelwahed Auhmani. (1S,3R,8R,11S)-2,2,11-Tribromo-10-bromomethyl-3,7,7-trimethyltricyclo[6.4.0.01,3]dodec-9-ene. IUCrData, 2016, 1 (5), pp.x160820. ⟨10.1107/S2414314616008208⟩. ⟨hal-02272735⟩