87687-54-5

Basic information

• Product Name: (+)-Isoclavukerin
• Synonyms: (+)-Isoclavukerin;(3aR)-2,3,3aβ,4,5,6-Hexahydro-1,4β-dimethylazulene;3,8α-Dimethyl-1,2,6,7,8,8aα-hexahydroazulene;(3aS)-2,3,3aα,4,5,6-Hexahydro-1,4β-dimethylazulene
• CAS NO: 87687-54-5
• Molecular Formula: C12H18
• Molecular Weight: 162.27132
• Mol File: 87687-54-5.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (+)-Isoclavukerin(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Isoclavukerin(87687-54-5)
• EPA Substance Registry System: (+)-Isoclavukerin(87687-54-5)

Safety Data

• Hazardous Substances Data: 87687-54-5(Hazardous Substances Data)

Upstream product

• 38231-11-7 (5S)-1-formyl-2-methyl-5-(1-methylethenyl)-1-cyclopentene 
• 162301-60-2 (6S,7S)-6,10-dimethylbicyclo<5.3.0>dec-1(10)-en-2-one toluene-p-sulfonylhydrazone 
• 74-85-1 ethene 
• 1259290-56-6 C₁₆H₂₆ 
• 909729-64-2 (-)-1αH,10αH-tri-nor-guaia-4,6-dien-3-one 
• 136264-89-6 (4S,6S)-3-<2-(ethoxycarbonyl)ethyl>-4-methyl-6-trimethylsilylcycloheptanone 

Downstream Products

• 87687-62-5 C₁₂H₁₈O₂ 

Relevant articles and documents

A bioinspired approach to Tri-nor-guaianes. Synthesis of (-)-clavukerin A

A bioinspired approach to tri-nor-guaianes by degradation of the C-7 side chain of related guaia-11-enes is described. In this approach (-)-clavukerin A (1) is obtained by selective ozonolysis-Criegge rearrangement of (+)-1α H,7αff,10αH-guaia-4,11-dien-3-one (4) to afford 7β-hydroxy and 7β-acetoxy tri-nor-guaiane derivatives 6 and 7, respectively, which after elimination and deoxygenation give the title compound. The starting guaiadienone is readly obtained from commercially available santonin or (+)-dihydrocarvone.

Enantioselective Synthesis of Guaianolides in the Osmitopsin Family by Domino Metathesis

Relay metathesis enabled an improved access from (S)-citronellal to the marine trisnorguaiane (-)-clavukerin A. This hydroazulene was applied as an advantageously functionalized building block for the asymmetric synthesis of the sesquiterpene lactone osmitopsin and the proposed structure of 4,5-epoxyosmitopsin using a chemo-, regio-, and diastereoselective diepoxide opening as the key step.

A concise catalytic route to the marine sesquiterpenoids (-)-clavukerin A and (-)-isoclavukerin A

Using a combined organocatalytic/metal-catalyzed strategy, the enantiopure title hydroazulenes were prepared in only four steps from (S)- and (R)-citronellal, respectively. A catalyst-controlled diastereoselective Michael addition of these aldehydes to methyl vinyl ketone followed by chemoselective dibromoolefination and one-pot Wittig olefination/alkyne formation afforded the key dienynes that underwent regioselective domino metathesis to yield the target natural products. A combination of an organocatalytic Michael addition and a ruthenium-catalyzed dienyne metathesis allowed efficient access to the enantiopure title hydroazulenes from (S)- and (R)-citronellal, respectively, in only four steps.