472986-71-3

Upstream product

• 472986-67-7 (E)-(S)-5-Methyl-1-((1R,2R)-4-methyl-2-triethylsilanyloxy-cyclohex-3-enyl)-hex-2-en-1-ol 
• 994-30-9 triethylsilyl chloride 
• 472986-69-9 (R)-((2R,3R)-3-Isobutyl-oxiranyl)-((1R,2R)-4-methyl-2-triethylsilanyloxy-cyclohex-3-enyl)-methanol 

Downstream Products

• 472986-72-4 1-((2S,3R)-3-Isobutyl-oxiranyl)-1-((1S,2R)-4-methyl-2-triethylsilanyloxy-cyclohex-3-enyl)-2-trimethylsilanyl-ethanol 
• 160299-94-5 (+)-cheimonophyllon E 
• 472986-74-6 (1R,6R)-6-[1-((2R,3R)-3-Isobutyl-oxiranyl)-vinyl]-3-methyl-cyclohex-2-enol 
• 472986-73-5 Triethyl-{(1R,6R)-6-[1-((2R,3R)-3-isobutyl-oxiranyl)-vinyl]-3-methyl-cyclohex-2-enyloxy}-silane 

Relevant academic research and scientific papers

Asymmetric total syntheses of (+)-cheimonophyllon E and (+)-cheimonophyllal

The highly enantiocontrolled total syntheses of natural (+)-cheimonophyllon E (5) and (+)-cheimonophyllal (6), biologically intriguing oxygenated bisabolane-type sesquiterpenoids, have been completed. The present synthetic strategy featured the use of an asymmetric aldol-type reaction for preparing in the first synthetic step an optically active 6-C-substituted 3-methyl-2-cyclohexenone derivative. Thus, a Mukaiyama aldol reaction of 1-methyl-3-silyloxy-1,3-cyclohexadiene 31 with α,β-unsaturated aldehyde 11 in the presence of a chiral (acyloxy)borane (CAB)-type Yamamoto catalyst 33 proceeded with high levels of both diastereo- and enantioselectivities. The predominant aldol adduct, syn-9, was transformed into γ,δ-epoxy allylic alcohol 8 by a nine-step sequence, including the substrate-controlled 1,2-reduction of enone, syn-12, also the epoxidation of allylic alcohol 15. Epoxy-alcohol 8 underwent 5-exo-cyclization in a high regioselective manner under acidic conditions to produce a bicyclic key intermediate (+)-7, which was eventually efficiently converted to (+)-cheimonophyllon E (5) or (+)-cheimonophyllal (6).