146204-97-9

Upstream product

• 106-24-1 Geraniol 
• 122-04-3 4-nitro-benzoyl chloride 
• 146338-69-4 {(2S,3S)-3-[2-((R)-3,3-Dimethyl-oxiranyl)-ethyl]-3-methyl-oxiranyl}-methanol 
• 82188-73-6 (2S,3S)-2,3-epoxygeraniol 
• 146204-96-8 4-Nitro-benzoic acid (2S,3S)-3-((S)-3-bromo-4-hydroxy-4-methyl-pentyl)-3-methyl-oxiranylmethyl ester 
• 146204-95-7 4-Nitro-benzoic acid (2S,3S)-3-methyl-3-(4-methyl-pent-3-enyl)-oxiranylmethyl ester 

Downstream Products

• 120293-93-8 methyl (2E,6E)-6,7;10,11-bisepoxy-3,7,11-trimethyl-2-dodecenoate 

Relevant academic research and scientific papers

Total syntheses of the squalene-derived halogenated polyethers ent-dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades

Herein we describe in full our investigations leading to the first total syntheses of ent-dioxepandehydrothyrsiferol and armatol A. Discovery of a bromonium-initiated epoxide-opening cascade enabled novel tactics for constructing key fragments found in both natural products and have led us to revise the proposed biogeneses. Other common features found in the routes include convergent fragment coupling strategies to assemble the natural products' backbones and the use of epoxide-opening cascades for rapid constructions of the fused polyether subunits. Through de novo synthesis of armatol A, we elucidate the absolute and relative configuration of this natural product.

Synthesis of four stereoisomers of the higher dipteran juvenile hormone III bisepoxide

The 6S,7S,10R-, 6S,7S,10S-, 6R,7R,10S-, and 6R,7R,10R-stereoisomers of the juvenile hormone III bisepoxide from higher Dipteran insects have been synthesised in high stereoisomeric purity. The route involves Sharpless epoxidation of geraniol to enantiomeric epoxyalcohols, which are each elaborated via separable diastereomeric bromohydrins.