60391-93-7

Usage

Uses

Used in Organic Synthesis:
(4E,8E)-dodeca-4,8-dienedial is used as a reagent in organic synthesis for the formation of heterocyclic compounds. Its unique structure allows for the creation of a wide range of complex molecules, making it a valuable tool in the field of chemistry.
Used in Fragrance and Flavor Industry:
(4E,8E)-dodeca-4,8-dienedial is used as a component in the production of fragrances and flavoring agents. Its ability to contribute to the overall scent and taste of various products makes it an important ingredient in the development of consumer goods.
Used in Agriculture:
(4E,8E)-dodeca-4,8-dienedial is used as an insecticide in the agricultural industry. Its insecticidal properties make it a potential candidate for the development of pest control products, helping to protect crops and increase agricultural yields.
Used in Pharmaceutical Research:
(4E,8E)-dodeca-4,8-dienedial is used as a precursor in the synthesis of bioactive molecules. Its potential anticancer activity has been studied, and it may contribute to the development of new drugs for the treatment of various diseases.

InChI:InChI=1/C12H18O2/c13-11-9-7-5-3-1-2-4-6-8-10-12-14/h3-6,11-12H,1-2,7-10H2/b5-3+,6-4+

Upstream product

• 676-22-2 (1E,5E,9E)-cyclododeca-1,5,9-triene 
• 131392-77-3 (4E,8E)-dodeca-4,8-diene-1,12-diol 
• 837382-45-3 trans,trans-5,9-Cyclododecadien-1,2-diol 
• 5202-25-5 (5E,9E)-(1R,2R)-Cyclododeca-5,9-diene-1,2-diol 

Downstream Products

• 122674-42-4 (5E,9E)-(1R,2S)-Cyclododeca-5,9-diene-1,2-diol 
• 5202-25-5 (5E,9E)-(1R,2R)-Cyclododeca-5,9-diene-1,2-diol 
• 909767-34-6 C₄₄H₅₈O₂Si₂ 
• 909767-35-7 cis-4-(tert-butyldiphenylsiloxy)-1-{5-[4-(tert-butyldiphenylsiloxy)-1-hydroxybutyl]tetrahydrofuran-2-yl}butan-1-ol 
• 909767-36-8 Acetic acid (S)-4-(tert-butyl-diphenyl-silanyloxy)-1-{(2S,5R)-5-[(R)-4-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-butyl]-tetrahydro-furan-2-yl}-butyl ester 
• 862557-80-0 (4R,5S,8S,9S,12R,13R)-5:8,9:12-dioxido-13-tert-butyldimethylsilyloxy-16-benzyloxy-hexadecan-1,4-olide 

Relevant academic research and scientific papers

Concise syntheses of the natural products (+)-sylvaticin and (+)-cis-sylvaticin

Two concise syntheses of the natural products cis-sylvaticin and sylvaticin are reported, using oxidative cyclization methodology as the key step. A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvaticin.

Synthesis of the non-adjacent bis-THF core of cis-sylvaticin using a double oxidative cyclisation

A short synthesis of the non-adjacent bis-THF core of the Annonaceous acetogenin cis-sylvaticin (1) is described. C2 Symmetrical (Z,E,E,Z)- and (E,E,E,E)-tetraenes 5 and 6 were synthesised in six and three steps respectively from (1E,5E,9E)-cyclododeca-1,5,9-triene. Subsequent permanganate promoted asymmetric bi-directional oxidative cyclisation of tetraene 5 was used to create the non-adjacent bis-THF core of 1, installing seven of the nine stereogenic centres present in the natural product in a single step. Desymmetrisation of the oxidative cyclisation product by mono-tosylation gave access to a C11-C32 fragment of cis-sylvaticin.

Total synthesis of cis-solamin: Exploiting the RuO4-catalyzed oxidative cyclization of dienes

An enantioselective total synthesis of cis-solamin has been accomplished using a highly diastereoselective ruthenium tetroxide catalyzed oxidative cyclization as a crucial transformation. Further key steps involved an enzymatic desymmetrization, a TPAP-catalyzed oxidative termini differentiation, and a ruthenium-catalyzed Alder-ene reaction. Thus, the total synthesis of cis-solamin was achieved in 11 steps with an overall yield of 7.5%.

Total synthesis of mucocin

The synthesis of the potent antitumor agent, mucocin, 1, was efficiently achieved in 20 steps from cyclodecatriene, thus confirming the proposed structure of this unusual member of the Annonaceous acetogenins. Demonstrating the power of the 'naked' carbon skeleton strategy, all seven asymmetric centers in the key fragment of the molecule were introduced by double AE reaction followed by double AD reaction. Simultaneous two ring closure reactions provided both the THP and THF rings in a single step.