(1S,3R,8S,9S,10R)-2,2-Dichloro-9,10-epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodecane and (1S,3R,8S,10R)-2,2-dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodecan-9-one

Abstract

The stereochemistries of the title compounds, both C(16)H(24)Cl(2)O, have been established by X-ray diffraction. In both structures, the seven-membered ring adopts the same conformation, whereas the six-membered ring shows an envelope conformation in the epoxydodecane structure and a boat conformation in the dodecan-9-one structure.

(1S,3R,8R)-2,2-Dibromo-3,7,7,10-tetramethyltricyclo[6.4.0.01,3]dodec-9-ene

“…For the reactivity of this sesquiterpene, see: Lassaba et al (1997); Chekroun et al (2000); El ; Sbai et al (2002); Dakir et al (2004). For its biological activity, see: Daoubi et al (2004).…”

(1S,2R,8R)-2,2-Dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.01,3]dodec-10-en-9-one

“…For the reactivity of this sesquiterpene, see: Lassaba et al (1998); Chekroun et al (2000); El ; Sbai et al (2002); Dakir et al (2004). For its biological activity, see: Daoubi et al (2004).…”

“…The reactivity of this sesquiterpene has been studied extensively by our team in order to prepare new products having biological proprieties (Lassaba et al, 1998;Chekroun et al, 2000;El Jamili et al, 2002;Sbai et al, 2002;Dakir et al, 2004). Indeed, these compounds were tested, using the food poisoning technique, for their potential antifungal activity against phytopathogen Botrytis cinerea (Daoubi et al, 2004).…”

“…Indeed, these compounds were tested, using the food poisoning technique, for their potential antifungal activity against phytopathogen Botrytis cinerea (Daoubi et al, 2004). Thus the action of one equivalent of dichlorocarbene, generated in situ from chloroform and in the presence of sodium hydroxide as base and n-benzyltriethylammonium chloride as catalyst, followed by epoxydation with m-chloroperbenzoic acid (m-CPBA) gives a mixture of two diasteroisomers:(1S,3R,8S,9S,10R)-2,2dichloro-9,10-epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.0 1,3 ]dodecane (X, 70%) and (1S,3R,8S,9R,10S)-2,2-dichloro-9,10epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.0 1,3 ]dodecane (Y, 30%) (Sbai et al, 2002). By treatment of the majority isomer (X) with hydrochloric acid (see experimental) we obtained the title compound in 70% yield.…”

1-Isopropyl-4,7-dimethyl-2,8-dinitronaphthalene

“…The reactivity of these sesquiterpenes and its derivatives has been studied extensively by our team in order to prepare new products having biological proprieties (Lassaba et al, 1998;Chekroun et al, 2000;El Jamili et al, 2002;Sbai et al, 2002;Dakir et al, 2004). Indeed, these compounds were tested, using the food poisoning technique, for their potential antifungal activity against the phytopathogen Botrytis cinerea (Daoubi et al, 2004).…”