70206-91-6

Upstream product

• 917-54-4 methyllithium 
• 202194-34-1 (2E,4E)-5-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-hexa-2,4-dienoic acid ethyl ester 
• 70224-50-9 (1S,3R,4R)-1-Acetyl-3-isopropenyl-4-methyl-4-vinylcyclohexane 
• 1301262-05-4 eunicol 
• 139694-39-6 (E)-3-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-but-2-enoic acid methyl ester 
• 139694-38-5 2-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-2-methyl-[1,3]dioxolane 
• 139694-47-6 (E)-3-((1S,4R,5R)-5-Isopropenyl-4-methyl-4-vinylcyclohex-1-yl)but-2-enal 
• 202194-29-4 (1R,2S,4R,5R)-2-Hydroxy-5-isopropenyl-4-methyl-4-vinyl-cyclohexanecarboxylic acid ethyl ester 
• 202194-28-3 (1R,4R,5R)-5-Isopropenyl-4-methyl-2-oxo-4-vinyl-cyclohexanecarboxylic acid ethyl ester 
• 202194-30-7 (4R,5R)-5-Isopropenyl-4-methyl-4-vinyl-cyclohex-1-enecarboxylic acid ethyl ester 
• 202194-37-4 (4R,5R)-5-Isopropenyl-4-methyl-4-vinylcyclohex-1-enecarboxylic acid 
• 202194-31-8 (4R,5R)-5-Isopropenyl-4-methyl-4-vinylcyclohexen-1-yl methyl ketone 
• 149404-74-0 (4R,5R)-1-Acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene 
• 139694-48-7 (2E,4E)-5-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-hexa-2,4-dienoic acid methyl ester 

Relevant academic research and scientific papers

Eunicidiol, an anti-inflammatory dilophol diterpene from Eunicea fusca

A new dilophol diterpene, eunicidiol (1), has been isolated from the crude extract of Eunicea fusca, a gorgonian coral collected from Hillsboro Ledge, Florida. This compound was purified, along with fuscol (2) and eunicol (3), using a combination of normal- and reversed-phase chromatography methods. The structure of eunicidiol (1) was elucidated by 1D and 2D NMR spectroscopic analysis, and the absolute configuration was assigned using Moshers method. The anti-inflammatory activity of 1-3 was evaluated by measuring their ability to reduce phorbol myristate acetate (PMA)-induced edema in a mouse ear model. Topical application of a 100 μg/ear dose of diterpenes 1-3 significantly reduced edema by 44%, 46%, and 54%, respectively. This activity was superior to indomethacin, a known anti-inflammatory used as a control.

Synthesis of beta-elemene, intermediates thereto, analogues and uses thereof

The present invention provides convergent processes for preparing beta-elemene, and analogues thereof. Also provided are analogues related to beta-elemene and intermediates useful for preparing the same. The present invention further provides novel compositions based on analogues of beta-elemene and methods for the treatment of cancer, such as brain tumor, lung cancer, colorectal cancer, gastric intestional cancer, and stomach cancer.

Synthetic study of marine lobane diterpenes: Efficient synthesis of (+)-fuscol

As part of a synthetic study on marine natural products, the enantioselective synthesis of (+)-fuscol 4, a representative lobane diterpene, has been achieved in 10 steps and ca. 20% overall yield from (4R,5R)-1-acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene 3b, which itself has been prepared as a building block directed toward the asymmetric synthesis of natural products, in more than 40% overall yield from (+)-nopinone 1.

Enantioselective total synthesis of β-elemene and fuscol based on enantiocontrolled Ireland-Claisen rearrangement

The potent antiinflammatory agent precursor (+)-fuscol (2) has been synthesized using the chiral reagent 1 to effect the key step, the completely enantioselective Ireland-Claisen rearrangement of ester 3 to acid 4a. Conversion of 4a to the corresponding aldehyde 4c, cation-olefin cyclization to 5a, and deoxygenation produced (+)-β-elemene (6). (+)-Fuscol (2) was synthesized from 6 via intermediates 7 and 8.

Total synthesis of marine diterpene fuscol

Marine diterpene fuscol was synthesized stereoselectively from D-mannitol via bicyclo[2.2.2]octane derivative 4, and its complete structure was established.