117952-72-4

Upstream product

• 534-00-9 (S)-2-methylbutyl bromide 
• 603-35-0 triphenylphosphine 
• 69097-01-4 (R)-4-bromo-3-methylbut-1-ene 
• 110659-28-4 (R)-(+)-5-acetoxy-4-methylpentanoic acid 
• 497-02-9 (E)-2-methyl-2-buten-1-ol 
• 57253-30-2 tiglyl bromide 
• 80-59-1 Tiglic acid 
• 110659-29-5 (R)-2-methyl-3-buten-2-yl tosylate 
• 110595-22-7 (R)-4-acetoxy-3-methyl-1-butene 
• 22644-30-0 (R)-2-methylbut-3-en-1-ol 

Relevant academic research and scientific papers

Total synthesis of infectopyrone, aplysiopsenes A-C, ent-aplysiopsene D, phomapyrones A and D, 8,9-dehydroxylarone, and nectriapyrone

The total synthesis of the 2-pyrone natural products nectriapyrone, aplysiopsenes A-C, ent-aplysiopsene D, phomapyrones A and D, and of 8,9-dehydroxylarone were achieved by Wittig olefination starting with vermopyrone. Infectopyrone was synthesized by Horner-Wadsworth-Emmons reaction starting with phomapyrone D. Racemic phomapyrone C methyl ether was obtained by hydrogenation of nectriapyrone. The total syntheses were achieved starting from commercially available 3,5-heptanedione and led to the desired natural products in 18-46% over 5-6 steps, whereupon all five-step syntheses were carried out with a single chromatographic workup. The total synthesis of infectopyrone, aplysiopsenes A-D, of phomapyrones A and D, and of 8,9-dehydroxylarone were achieved for the first time, giving unambiguous proof for the proposed structures of these natural products.