(+)-Isoclavukerin

Base Information

• Chemical Name: (+)-Isoclavukerin
• CAS No.: 87687-54-5
• Molecular Formula: C12H18
• Molecular Weight: 162.27132
• Mol file: 87687-54-5.mol

Synonyms:(8S,8aS)-3,8-Dimethyl-1,2,6,7,8,8a-hexahydro-azulene;Clavukerin A;(-)-clavukerin A;

Chemical Property of (+)-Isoclavukerin

Chemical Property:

• PSA: 0.00000
• LogP: 3.69900

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (+)-Isoclavukerin

There total 48 articles about (+)-Isoclavukerin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

C21H34 → (-)-1αH,10αH-tri-nor-guaia-4,6-diene (87687-54-5)

Guidance literature:

C₂₁H₃₄; With Grubbs catalyst first generation; In dichloromethane; Reflux; Inert atmosphere;

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; Reflux; Inert atmosphere;

DOI:10.1021/acs.orglett.6b01619

Reference yield: 92.0%

C21H34 → C12H18 (1259290-59-9) + (-)-1αH,10αH-tri-nor-guaia-4,6-diene (87687-54-5)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; p-benzoquinone; In dichloromethane; for 4h; Reflux; Inert atmosphere;

DOI:10.1021/acs.orglett.6b01619

Reference yield: 85.0%

(S)-2-Methyl-5-((S)-1-methyl-4-oxo-butyl)-cyclopent-1-enecarbaldehyde (181782-14-9) → (-)-1αH,10αH-tri-nor-guaia-4,6-diene (87687-54-5)

Guidance literature:

With titanium tetrachloride; zinc; In tetrahydrofuran; Heating; syringe pump, 16 h, reverse addition;

DOI:10.1016/0040-4039(96)01279-8

upstream raw materials:

(6S,7S)-6,10-dimethylbicyclo<5.3.0>dec-1(10)-en-2-one toluene-p-sulfonylhydrazone

(S)-2-Methyl-5-((S)-1-methyl-4-oxo-butyl)-cyclopent-1-enecarbaldehyde

(4R)-limonene 1,2-epoxide

(5S)-1-formyl-2-methyl-5-(1-methylethenyl)-1-cyclopentene

Downstream raw materials:

C₁₂H₁₈O₂

Refernces

Total Synthesis of Clavukerin A and Its Epimer

10.1246/cl.1991.1295

The study details the enantioselective total synthesis of clavukerin A and its epimer. Clavukerin A is a trisnorsesquiterpenoid compound initially isolated from the Okinawan soft coral Clavularia koellikeri, while its epimer was isolated from an Australian soft coral Cespitularia sp. The researchers aimed to synthesize these compounds to clarify their relationship and contribute to understanding their biogenetic pathways. The synthesis began with optically pure (-)-4, derived from cyclohexenone (+)-3. Through a series of reactions involving zinc homoenolates, diastereoisomers (-)-6a and (-)-6b were formed. These were then converted to enones (-)-9a and (-)-9b via desilylation, reduction, and hydrogenation steps. The enones underwent intramolecular aldol-type condensation to form (-)-9a and (-)-9b. The final conversion to the desired compounds was achieved using the Shapiro reaction, yielding clavukerin A and its epimer. The synthesized compounds were confirmed to be identical to the natural ones through comparison of spectral data and specific rotations.

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