38236-17-8

Usage

Uses

Given the limited information available on the compound's applications, the following uses are speculative based on its chemical class and structure:
Used in Pharmaceutical Industry:
Azuleno[4,5-b]furan-2(3H)-one,3a,4,5,6,6a,7,9a,9b-octahydro-3,9-dimethyl-6-methylene-, (3S,3aS,6aR,9aR,9bS)could potentially be used as a pharmaceutical intermediate or a lead compound for the development of new drugs. Its complex structure and chirality may offer unique biological activities or interactions with biological targets, warranting further research and exploration.
Used in Chemical Synthesis:
Due to its azulenone core and multiple functional groups, the compound may serve as a building block or a key intermediate in the synthesis of more complex organic molecules. It could be utilized in the preparation of novel compounds with potential applications in various fields, such as materials science, agrochemicals, or specialty chemicals.
Used in Research and Development:
Azuleno[4,5-b]furan-2(3H)-one,3a,4,5,6,6a,7,9a,9b-octahydro-3,9-dimethyl-6-methylene-, (3S,3aS,6aR,9aR,9bS)-'s unique structure and chirality may be of interest to researchers studying the synthesis, properties, and reactivity of complex organic molecules. It could be employed as a model compound to investigate new synthetic methods, reaction mechanisms, or stereoselective processes.

Upstream product

• 69075-77-0 gallicin 
• 124-63-0 methanesulfonyl chloride 
• 68421-48-7 4α-hydroxy-1α,5α,6β,7α,11α-H-guaian-10(15)-en-6,12-olide 
• 17946-95-1 (3S,3aS,6R,6aR,9aR,9bS)-6-Hydroxy-3,6,9-trimethyl-3a,4,5,6,6a,7,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one 
• 481-06-1 santonin 
• 38236-17-8 grilactone 
• 67895-32-3 (11S)-3α-(benzoyloxy)-1β-(mesyloxy)eudesmano-13,6α-lactone 
• 67895-31-2 (11S)-3α-(benzoyloxy)-1β-hydroxyeudesmano-13,6α-lactone 
• 82691-62-1 (11S)-1,1-(ethylenedioxy)-3-oxoeudesmano-13,6α-lactone 
• 67895-26-5 (11S)-1,1-(ethylenedioxy)-3α-hydroxyeudesm-4(14)-eno-13,6α-lactone 
• 66260-85-3 (11S)-1,1-(ethylenedioxy)eudesm-3-eno-13,6α-lactone 
• 67895-32-3 Benzoic acid (3S,3aS,5aR,6R,8R,9R,9aS,9bS)-6-methanesulfonyloxy-3,5a,9-trimethyl-2-oxo-dodecahydro-naphtho[1,2-b]furan-8-yl ester 
• 67895-33-4 (11S)-3α-(benzoyloxy)-4βH-guai-10(14)-eno-13,6α-lactone 
• 82207-05-4 (11S)-3α-hydroxy-4βH-guai-10(14)-en-13,6α-lactone 

Downstream Products

• 67895-37-8 (11S)-1α-hydroxyguaia-3,10(14)-dieno-13,6α-lactone 
• 82263-12-5 (+)-3α,4α-epoxy-1,5,7αH,6,11βH-guai-1(14)-en-6,12-olide 
• 68151-26-8 isodehydrocostus lactone 
• 38236-17-8 (3R,3aR,6aR,9aR,9bS)-3,9-Dimethyl-6-methylene-3a,4,5,6,6a,7,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one 
• 529-05-5 chamazulene 
• 75253-74-6 C₁₅H₁₈O₃ 
• 87606-11-9 (-)-gochnatiolides B 
• 1089724-16-2 (-)-ainsliadimer B 
• 87606-12-0 (-)-gochnatiolides A 
• 1390642-54-2 C₃₀H₂₈O₇ 

Relevant academic research and scientific papers

A biomimetic total synthesis of (+)-ainsliadimer A

Figure Presented. A protecting group free and biomimetic total synthesis of (+)-ainsliadimer A has been accomplished in 14 steps from α-santonin. The synthesis relies on a hydrogen bonding promoted [4 + 2]-hetero-Diels-Alder dimerization to afford the key homodimer intermediate, which demonstrates the feasibility of using nonenzymatic conditions to achieve the proposed biosynthesis.

Guaianolides as immunomodulators. Synthesis and biological activities of dehydrocostus lactone, mokko lactone, eremanthin, and their derivatives

The naturally occurring guaianolides, namely mokko lactone (1), dehydrocostus lactone (2), eremanthin (3), and related guaianolides, 16, 17, 21, 22, 28-31, 33, 36, 37, and 39, have been synthesized starting from l-α- santonin in an effort to examine their structure-activity relationship as inhibitors of the killing function of cytotoxic T lymphocytes (CTL) and the induction of intercellular adhesion molecule-1 (ICAM-1). It was observed during the present study that the guaianolides possessing an α-methylene γ- lactone moiety, i.e., 2, 3, 30, 33, 37, and 39, exhibited significant inhibitory activity toward the killing function of CTL and the induction of ICAM-1.

Regio- and stereoselective oxyfunctionalization at C-1 and C-5 in sesquiterpene guaianolides

The regio- and stereoselective functionalization at C-1 and C-5 positions in a guaiane skeleton by allylic hydroxylation are described. The stereochemistry of the resulting compounds are identical to those of the majority of natural 1- and 5-hydroxy-guaianolides.

Synthesis (in ent-form) of a Novel Jalcaguaianolide from Ferula arrigonii Bocchieri

A recently isolated isodehydrocostus lactone from the genus Ferula (Umbelliferae) has been stereoselectively prepared from ent-form from α-santonin by a photochemical transformation to O-acetylisophotosantonic lactone followed by functional group manipulations that conclude with a one-step γ-butyrolactone -> Δα,β-butenolide conversion; the synthesis corroborates both the structure and the relative and absolute stereochemistry that have been proposed for the natural product.

Syntheses of Four Possible Diastereoisomers of Bohlmann's Structure of Isoepoxyestafiatin. The Stereochemical Assignment of Isoepoxyestafiatin

The stereochemistry of isoepoxyestafiatin was determined to be 1β,10β:3α,4α-diepoxyguaia-11(13)-eno-12,6α-lactone by the syntheses of the four possible diastereoisomers 23-26.

Studies on the Syntheses of Sesquiterpene Lactones. 11. The Syntheses of 3-Epizaluzanin C, Zaluzanin C, Zaluzanin D, and Related Compounds 3&α-Hydroxyguaia-1(10),4(15),11(13)-trieno-12,6&α-lactone and 3&α-Hydroxyguaia-4(15),9,11(13)-trieno-12,6&α-lactone

3-Epizaluzanin C (10), 3α-hydroxyguaia-1(10),4(15),11(13)-trieno-12,6α-lactone (36), and 3α-hydroxyguaia-4(15),9,11(13)-trieno-12,6α-lactone (37) have been synthesized in 4.0percent, 3.0percent, and 1.7percent overall yields, respectively, from α-santonine (13) in 14 steps.Zaluzanin C (11) and zaluzanin D (12) have also been synthesized in 2.4percent and 2.5percent overall yields from α-santonin (13) in 16 steps and 15 steps, respectively.The key step involves the solvolytic rearrangement of (11S)-3α,4α-epoxy-1β-(mesyloxy)eudesmano-13,6α-lactone (27).The stereochemistry of3-epizaluzanin C (10), zaluzanin C (11), and zaluzanin D (12) have been established by these stereospecific syntheses.

THE BIOMIMETIC SYNTHESIS OF TRANS-(1β-H,5α-H)-GUAIANOLIDES

1-epigallicin 11 underwent biomimetic cyclization to trans-(1β-H,5α-H)-guaianolide 22, the stereoespecificity of this cyclization being credited to the fact that it took place via the reacting TC conformation 27.The epimeric nor-guaianolides 15 and 17 were prepared and their rearrangements studied.The biogenetic implications of these processes are discussed.

TOTAL SYNTHESIS OF ZALUZANIN C, ZALUZANIN D, AND 3-EPIZALUZANIN C

The biologically active guaianolides, zaluzanin C, and zaluzanin D, and the stereoisomeric guaianolide, 3-epizaluzanin C have been synthesized by two different procedures.The stereochemistry at C3 of zaluzanin C has been established to be S configuration by this synthesis.

Biomimetic cyclization of gallicin to form guaianolides1 1 Part 43 in the series Chemistry of the Composites. For Part 42, see: A.G. Gonzalez, A. Galindo, H. Mansilla and A. Alemany, Tetrahedron Letters 376

A biomimetic-type cyclization of gallicineas carried out to form guaianolides. The possible mechanism is discussed and the stereoselectivity of the reaction explained by a preferred reacting conformation.