171291-29-5

Upstream product

• 110202-07-8 (E)-4-Methyl-6-(2',6',6'-trimethyl-1'-cyclohexenyl)hex-3-en-1-ol 

Downstream Products

• 261522-00-3 (E)-2-((R)-3-Furan-3-yl-3-hydroxy-propionyl)-6-methyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-oct-5-enoic acid methyl ester 
• 539802-71-6 (+)-(1R)-(3Z,7E)-4-iodo-8-methyl-1-(5'-triethylsilylfuran-3'-yl)-10-(2'',6'',6''-trimethylcyclohex-1-enyl)deca-3,7-dien-1-ol 
• 539802-73-8 (+)-(6R)-3-[(E)-4'-methyl-6'-(2'',6'',6''-trimethylcyclohex-1''-enyl)hex-3'-enyl]-6-(5'''-triethylsilylfuran-3'''-yl)-5,6-dihydropyran-2-one 
• 540482-87-9 (+)-(R)-manoalide 

Relevant academic research and scientific papers

Synthesis of (+)-manoalide via a copper(I)-mediated 1,2-metalate rearrangement

An enantiospecific synthesis of the phospholipase A2 inhibitor (+)-(4R)-manoalide is reported in which all 25 carbons of the sesterterpenoid skeleton are constructed from 3-furaldehyde, trimethylalane, oxirane, CO, β-ionone, and propargyl bromide. The overall yield for the longest linear sequence (12 steps) is 12%. Key steps include (a) a zirconium-catalyzed carboalumination reaction to construct the C10-C11 trisubstituted alkene, (b) a Cu(I)-mediated 1,2-metalate rearrangement to construct the C6-C7 trisubstituted alkene, (c) a Sharpless kinetic resolution to secure the (4R)-stereochemistry, (d) generation of a 5-stannyl-2,3-dihydrofuran by Mo-catalyzed cycloisomerization of a homopropargylic alcohol, and (e) construction of the hydroxyfuranone ring by photooxidation of a silylfuran.