26931-87-3

Usage

Uses

Used in Pharmaceutical Industry:
(3aS,4R,5Z,9E,11aS)-3a,4,7,8,11,11a-Hexahydro-4-hydroxy-6-hydroxymethyl-10-methyl-3-methylenecyclodeca[b]furan-2(3H)-one is used as a pharmaceutical compound for its potential therapeutic properties. The presence of hydroxyl and methyl groups, along with the lactone ring, may contribute to its biological activity and interactions with biological targets.
Used in Biochemistry Research:
(3aS,4R,5Z,9E,11aS)-3a,4,7,8,11,11a-Hexahydro-4-hydroxy-6-hydroxymethyl-10-methyl-3-methylenecyclodeca[b]furan-2(3H)-one is used as a research tool in biochemistry to study the interactions between small molecules and biological systems. Its unique structure and functional groups may provide insights into molecular recognition and binding processes.
Used in Organic Chemistry Synthesis:
(3aS,4R,5Z,9E,11aS)-3a,4,7,8,11,11a-Hexahydro-4-hydroxy-6-hydroxymethyl-10-methyl-3-methylenecyclodeca[b]furan-2(3H)-one is used as a synthetic intermediate in organic chemistry for the preparation of more complex molecules. Its versatile structure and functional groups make it a valuable building block for the synthesis of various organic compounds.

InChI:InChI=1/C15H20O4/c1-9-4-3-5-11(8-16)7-12(17)14-10(2)15(18)19-13(14)6-9/h4,7,12-14,16-17H,2-3,5-6,8H2,1H3/b9-4+,11-7-/t12-,13+,14+/m1/s1

Upstream product

• 26931-94-2 salonitenolide 

Downstream Products

• 22391-22-6 isabelin 
• 22553-66-8 (+)-β-cyclopyrethrosin 

Relevant academic research and scientific papers

Acid-induced rearrangement of Epoxygermacra-8, 12-olides: Synthesis and absolute configuration of guaiane and eudesmane derivatives from Artemisiifolin

A study on the acid-induced, rearrangement of 4, 5-epoxyand l, 10-epoxygermacra-8, 12-olides was carried out. From a 4, 5-epoxy derivative, guaianes were obtained, whereas 1, 10-epoxy derivatives furnished, depending on the stereochemistry of the C-1-/C-10 epoxy ring, trans-5ss, 10α- or trans-5α, 10sseudesmanolides.

15-Hydroxygermacranolides as Sources of Structural Diversity: Synthesis of Sesquiterpene Lactones by Cyclization and Rearrangement Reactions. Experimental and DFT Study

A study on the electrophile-induced rearrangement of two 15-hydroxygermacranolides, salonitenolide and artemisiifolin, was carried out. These compounds underwent electrophilic intramolecular cyclizations or acid-mediated rearrangements to give sesquiterpene lactones with different skeletons such as eudesmanolides, guaianolides, amorphanolides, or other germacranolides. The cyclization that gives guaianolides can be considered a biomimetic route to this type of sesquiterpene lactones. The use of acetone as a solvent changes the reactivity of the two starting germacranolides to the acid catalysts, with a 4,15-diol acetonide being the main product obtained. The δ-amorphenolide obtained by intramolecular cyclization of this acetonide is a valuable intermediate for accessing the antimalarials artemisinin and its derivatives. Mechanistic proposals for the transformations are raised, and to provide support them, quantum chemical calculations [DFT B3LYP/6-31+G(d,p) level] were undertaken.

Unified synthesis of eudesmanolides, combining biomimetic strategies with homogeneous catalysis and free-radical chemistry

(Matrix presented) A general procedure for the synthesis of both 12,6- and 12,8-eudesmanolides has been developed. The key step is the titanocene-catalyzed radical cyclization of accessible epoxygermacrolides. The novel reagent 2,4,6-trimethyl-1-trimethylsilylpyridinium chloride, both compatible with oxiranes and capable of regenerating Cp2TiCl 2 from Cp2Ti(Cl)H and Cp2Ti(Cl)OAc, played an important role in the catalytic cycle leading to exocyclic alkenes.