Synthesis of (.+-.)-rubrynolide and a revision of its reported stereochemistry

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).…”

“…Thus, epoxides are important precursors in the synthesis of Antifungal products (Taylor et al, 1991) and different pheromones (Mori, 1989, Paddon-Jones et al, 1997. Besides, many natural products possess this functional group as an essential structural moiety for their biological activities (Yang, 2004;Vollhardt & Schore, 1996;Trost et al, 1983).…”

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

“…For the use of epoxydes in organic synthesis, see: Mori (1989); Paddon-Jones et al (1997); Taylor et al (1991). For their biological activity, see: Kupchan et al (1989); Trost et al (1983); Vollhardt & Schore (1996); Yang (2004).…”

“…E70, o480 Epoxides are important synthetic intermediates that are widely used in organic synthesis. They are described in the synthesis of Antifungal products (Taylor et al, 1991) and different pheromones (Mori, 1989, Paddon-Jones et al, 1997.…”

Spiro γ-Lactones via Aluminum Enolate-Spiroepoxide Openings

“…9 The utility of the aluminum enolate route to lactones was demonstrated by featuring it as the key step in a short synthesis of (±)-rubrynolide. 10 In the present work, we have extended the aluminum enolate methodology to spiro epoxides 8 which provides tertiary hydroxy esters 10 that yield spiro γ -lactones 11 upon treatment with acid (Scheme). The spiroepoxides 8 are readily obtained from their respective olefins via epoxidation or from treatment of the appropriate ketone with a sulfur ylide.…”