82398-57-0

Upstream product

• 372-97-4 farnesyl pyrophosphate 
• 2385-77-5 (R)-Citronellal 
• 1232772-99-4 (R)-8,8-dibromo-2,6-dimethyloct-2-ene 
• 1449248-33-2 (R)-6,6-dibromo-4-methylhexanal 
• 1449248-28-5 (R,E)-4-methylnon-7-en-2-yn-1-ol 
• 1449248-35-4 (R,E)-4-methylnon-7-en-2-ynyl 4-methylbenzenesulfonate 
• 1449248-36-5 (R,E)-tert-butyldimethyl(2,2,5-trimethyl-4-vinylidenedec-8-enyloxy)silane 
• 1449248-40-1 (R,E)-2,2,5-trimethyl-4-vinylidenedec-8-en-1-ol 
• 1449248-37-6 (E)-2,2,5-trimethyl-4-vinylidenenedec-8-enal 
• 94904-15-1 (3aR,4S,5S,5aS,8R,8aS)-2,2,5,8-tetramethyldecahydrocyclopentapentalen-4-ol 
• 1449248-38-7 C₁₅H₂₄O 
• 83110-20-7 (1S,2S,6S,8R,9R)-1,4,4-Trimethyl-12-oxa-tricyclo[7.2.1.0^2,6]dodecan-8-ol 
• 83110-21-8 (1S,2S,6S,8R,9R)-8-Bromo-1,4,4-trimethyl-12-oxa-tricyclo[7.2.1.0^2,6]dodecane 
• 83110-19-4 (1S,2S,6S,9R)-1,4,4-Trimethyl-12-oxa-tricyclo[7.2.1.0^2,6]dodecan-8-one 

Relevant academic research and scientific papers

A CONVERSION OF HUMULENE TO HIRSUTENE

Humulene has been transformed into 1,4,4-trimethyltricyclo-2,6>undecan-11-one, a key intermediate for the synthesis of hirsutene, through a process which simulates the biosynthetic pathway assumed for the latter sesquiterpene.

Mechanistic Similarities of Sesquiterpene Cyclases PenA, Omp6/7, and BcBOT2 Are Unraveled by an Unnatural fPP-Ether Derivative

The sesquiterpene cyclases pentalenene synthase (PenA) and two Δ6-protoilludene synthases Omp6 and Omp7 convert a FPP ether into several new tetrahydrofurano terpenoids, one of which is also formed as the main product by the sesquiterpene cyclase BcBOT2. Thus, PenA, Omp6/7, and BcBOT2 follow closely related catalytic pathways and induce similar folding of their diphosphate substrates despite low levels of amino acid sequence similarity. Some of the new terpenoids show pronounced olfactoric properties.

Exploiting the Synthetic Potential of Sesquiterpene Cyclases for Generating Unnatural Terpenoids

The substrate flexibility of eight purified sesquiterpene cyclases was evaluated using six new heteroatom-modified farnesyl pyrophosphates, and the formation of six new heteroatom-modified macrocyclic and tricyclic sesquiterpenoids is described. GC-O analysis revealed that tricyclic tetrahydrofuran exhibits an ethereal, peppery, and camphor-like olfactoric scent.

An asymmetric total synthesis of (+)-pentalenene

A stereoselective total synthesis of (+)-pentalenene was achieved through the tandem cycloaddition reaction of the allenyl diazo substrate prepared from (+)-citronellal. The initial intramolecular [2+3] cycloaddition reaction between the diazo functionality and the allenyl group produced the trimethylenemethane (TMM) intermediate after immediate loss of nitrogen molecule from the cycloaddition intermediate. Subsequent [2+3] cycloaddition of the TMM with olefin produced the angularly fused triquinane structure stereoselectively.

Effect of isotopically sensitive branching on product distribution for pentalenene synthase: Support for a mechanism predicted by quantum chemistry

Mechanistic proposals for the carbocation cascade reaction leading to the tricyclic sesquiterpene pentalenene are assessed in light of the results of isotopically sensitive branching experiments with the H309A mutant of pentalenene synthase. These experimental results support a mechanism for pentalenene formation involving a 7-protoilludyl cation whose intermediacy was first predicted using quantum-chemical calculations.