(1S,3S,8R,9S)-3,7,7,10-Tétraméthyl-9-[(1S,3S,8R,9S)-3,7,7-triméthyl-10-méthylènetricyclo[6,4,0,0^1,3]dodéc-9-yloxy]tricyclo[6,4,0,0^1,3]dodéc-10-ène

Abstract

The stereochemistry of the product resulting from the rearangement of (1S,3R,8R,9R,10R)‐9,10‐epoxy‐3,7,7,10‐tetramethyltricyclo[6,4,0,01,3]dodecane has been established by X‐ray crystallography. The molecule, C32H50O, is composed of two distinct parts linked by a dioxo bond. In each part of the molecule, the conformation of the six‐membered ring is imposed by the position of the double bond.

Screening Study of Lead Compounds for Natural Product-Based Fungicides: Antifungal Activity and Biotransformation of 6α,7α-Dihydroxy-β-himachalene byBotrytis cinerea

“…The reactivity of himachalene sesquiterpenes has been extensively studied. Compounds 2 − 12 ( Figure ) were obtained following procedures previously described ( − ). The “poisoned food technique” was used to determine the antifungal properties of the compounds under study ( , ).…”

“…Compounds 1 − 12. β-Himachalene ( 1 ) was isolated from the essential oil of the Atlas cedar ( Cedrus atlantica ) collected in Morocco. Compounds 2 − 12 ( Figure ) were synthesized following the procedures previously reported ( − ).…”

(1S,3S,8R,9S,10R)-9,10-Epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.01,3]dodecane

“…For structural discussion, see: Cremer & Pople (1975); Flack (1983); Flack & Bernardinelli (2000); Spek (2009); Boessenkool & Boyens (1980); Benharref et al (2010). For the synthesis, see: Auhmani et al (2001).…”

“…In order to prepare new epoxides with natural products, we synthesized (1S,3S,8R,9S,10R)-9,10-epoxy-3,7,7,10-tetramethyltricyclo [6.4.0.0 1,3 ]dodecane in three stages from β-himachalene. The title compound was prepared by treating (1S,3S,8R)-3,7,7,10-tetramethyltricyclo[6.4.0.0 1,3 ]dodec-9-ene (Auhmani et al, 2001) by metachloroperbenzoique acide.…”