(1S,3S,8R,9S,10R)-9,10-Epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodecane

Abstract

The title compound, C16H26O, was synthesized by treating (1S,3S,8R)-3,7,7,10-tetra­methyl­tri­cyclo­[6.4.0.01,3]dodec-9-ene with meta­chloro­perbenzoic acid. The mol­ecule is built up from two fused six- and seven-membered rings. The six-membered ring has a half-chair conformation, whereas the seven-membered ring displays a boat conformation. In the crystal, there are no significant intermolecular interactions present.

Synthesis and Biological Evaluation of Novel Thiazole Analogs with Both Anti‐Proliferative and Mechanistic Analyses and Molecular Docking Studies

“…The targeted thio-and semicarbazones derivatives as well as the 1,3-thiazoles were prepared from the naturally occurring βhimachalene (isolated from Cedrus Atlantica essential oil [36] ) as depicted in Scheme 1. The first step involved the [1 + 2] ChemistrySelect cycloaddition reaction between β-himachalene 1 and dichloro-/dibromocarbenes to give compounds 2 a-b.…”

Crystal structure of (1R,3S,8R,11R)-11-acetyl-3,7,7-trimethyl-10-oxatricyclo[6.4.0.01,3]dodecan-9-one

“…For biological activities of terpenic lactones, see: Hall et al (1987); Ohnishi et al (1997); Ghosh & Karin (2002); Bremner & Heinrich (2002); Francois et al (1996); Rabe et al (2002); Calera et al (1995). For the synthesis, see: Bimoussa et al (2014). For the ring puckering parameters, see: Boessenkool & Boyens (1980).…”

“…Thus, In order to prepare new lactones using natural products, we have prepared (1R,3S,8R,11R)-11-acetyl-3,7,7-trimethyl-10-oxatricyclo[6.4.0.0 1,3 ]dodecan-9-one from β-himachalène (sesquiterpenic hydrocarbon). The title compound was prepared by an oxidative cleavage of (1S,3S,8R,9S,10R)-9,10-Epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.0 1,3 ]dodecane (Bimoussa et al, 2014) using periodic acid as oxydant.…”

Crystal structure of (1R,2S,4R,7R,8S,9R)-3,3-dichloro-8,9-epoxy-4,8,12,12-tetramethyltricyclo[5.5.0.02,4]dodecane

“…For applications of epoxides, see: Qu et al (2009); Taylor et al (1991); Mori (1989); Paddon-Jones et al (1997); Yang (2004); Vollhardt & Schore (1996); Trost et al (1983). For related structures, see: Chiaroni et al (1992Chiaroni et al ( , 1995Chiaroni et al ( , 1996a; Sbai et al (2002); Benharref et al (2010); Oukhrib et al (2013); Bimoussa et al (2014). For puckering parameters and ring conformation, see: Boessenkool & Boeyens (1980 Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al, 1999); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2013.…”

“…A search in the Cambridge Structural Database, version 5.36 reveals 9 hits with related structure having two fused 6 and 7 membered rings (Chiaroni et al, 1992(Chiaroni et al, , 1995Chiaroni et al, 1996a,b,c;Sbai et al, 2002;Benharref et al, 2010;Oukhrib et al, 2013;Bimoussa et al, 2014 )…”