540482-87-9

Upstream product

• 171291-29-5 2-[(E)-6-iodo-3-methylhex-3-enyl]-1,3,3-trimethylcyclohexene 
• 110202-07-8 (E)-4-Methyl-6-(2',6',6'-trimethyl-1'-cyclohexenyl)hex-3-en-1-ol 
• 261522-05-8 (R)-6-Furan-3-yl-3-[(E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hex-3-enyl]-5,6-dihydro-2H-pyran-2-ol 
• 80388-50-7 seco-manoalide 
• 261522-03-6 Acetic acid (4S,6R)-6-furan-3-yl-3-[(E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hex-3-enyl]-2-oxo-tetrahydro-pyran-4-yl ester 
• 261522-04-7 (R)-6-Furan-3-yl-3-[(E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hex-3-enyl]-5,6-dihydro-pyran-2-one 
• 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 

Downstream Products

• 75088-81-2 manoalide 25-acetal monoacetate 
• 75088-83-4 manoalide 25-acetals diacetate 
• 121402-07-1 luffariolide B 

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.

First enantioselective synthesis of manoalide: Application of aldehyde- dioxinone enantioselective condensation

Manoalide, an analgesic and anti-inflammatory sesterterpene, has been stereoselectively synthesized for the first time. The C-4 stereogenic centre has been introduced in an early step by enantioselective aldol condensation using a Ti(OiPr)4/(R)

THREE NEW SESTERTERPENOID ANTIBIOTICS FROM THE MARINE SPONGE LUFFARIELLA VARIABILIS (POLEJAFF)

Structures of three new sesterterpenoid antibiotics 2, 3 and 4, isolated from a marine sponge have been determined by spectral analysis and chemical transformations.