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Technology Process of Gambierol

Gambierol

Base Information
  • Chemical Name:Gambierol
  • CAS No.:146763-62-4
  • Molecular Formula:C43H64O11
  • Molecular Weight:756.975
  • Hs Code.:
  • UNII:844Q8WC5F6
  • DSSTox Substance ID:DTXSID30880110
  • Nikkaji Number:J1.025.120F
  • Wikipedia:Gambierol
  • Wikidata:Q30594796
  • Metabolomics Workbench ID:177005
  • ChEMBL ID:CHEMBL266438
Gambierol

Synonyms:gambierol

Suppliers and Price of Gambierol
Supply Marketing:
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
Total 2 raw suppliers
Chemical Property of Gambierol
Chemical Property:
  • Vapor Pressure:1.87E-31mmHg at 25°C 
  • Boiling Point:823.7°C at 760 mmHg 
  • Flash Point:452°C 
  • PSA：134.53000 
  • Density:1.18g/cm3 
  • LogP:4.93590 
  • XLogP3:3.5
  • Hydrogen Bond Donor Count:3
  • Hydrogen Bond Acceptor Count:11
  • Rotatable Bond Count:7
  • Exact Mass:756.44486285
  • Heavy Atom Count:54
  • Complexity:1470
Purity/Quality:

99% *data from raw suppliers

Safty Information:
  • Pictogram(s):  
  • Hazard Codes: 
MSDS Files:

SDS file from LookChem

Useful:
  • Canonical SMILES:CC12CC3C(CC4C(O3)CCC5C(O4)(CC6(C(O5)CC7C(O6)C=CC(C(O7)C=CC=CCC=C)(C)O)C)C)OC1CC8C(O2)(C(CC(O8)CCCO)O)C
  • Isomeric SMILES:C[C@@]12C[C@H]3[C@@H](C[C@H]4[C@H](O3)CC[C@H]5[C@](O4)(C[C@]6([C@H](O5)C[C@H]7[C@H](O6)C=C[C@]([C@H](O7)/C=C\C=C/CC=C)(C)O)C)C)O[C@H]1C[C@@H]8[C@@](O2)([C@H](C[C@@H](O8)CCCO)O)C
Technology Process of Gambierol

There total 9 articles about Gambierol 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: 85.0%

C<sub>38</sub>H<sub>57</sub>IO<sub>11</sub>

C38H57IO11

(Z)-1-tributylstannyl-1,4-pentadiene
213815-44-2,466696-62-8

(Z)-1-tributylstannyl-1,4-pentadiene

Gambierol
146763-62-4

Gambierol

Guidance literature:
With copper(l) iodide; P(furyl)3; tris-(dibenzylideneacetone)dipalladium(0); In dimethyl sulfoxide;
DOI:10.1002/chem.200500994

Reference yield: 84.0%

C<sub>38</sub>H<sub>57</sub>IO<sub>11</sub>

C38H57IO11

(Z)-1-tributylstannyl-1,4-pentadiene
213815-44-2,466696-62-8

(Z)-1-tributylstannyl-1,4-pentadiene

(32E)-gambierol

(32E)-gambierol

Gambierol
146763-62-4

Gambierol

Guidance literature:
With copper(l) chloride; lithium chloride; tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; dimethyl sulfoxide; at 20 ℃;
DOI:10.1002/chem.200400355

Reference yield: 72.0%

(Z)-1-tributylstannyl-1,4-pentadiene
213815-44-2,466696-62-8

(Z)-1-tributylstannyl-1,4-pentadiene

C<sub>38</sub>H<sub>57</sub>IO<sub>11</sub>

C38H57IO11

Gambierol
146763-62-4

Gambierol

Guidance literature:
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; copper(l) iodide; P(furyl)3; In dimethyl sulfoxide; at 40 ℃; for 16h;
DOI:10.1021/ja028726d
upstream raw materials:

(Z)-1-tributylstannyl-1,4-pentadiene

C38H57BrO11

C53H91IO11Si2

C66H103BrO11Si3

Refernces

Total synthesis of gambierol

10.1021/ol9017408

Hiroki Furuta, Yuki Hasegawa, and Yuji Mori from Meijo University, Japan, describes the successful total synthesis of gambierol, a neurotoxin isolated from the dino?agellate Gambierdiscus toxicus. The authors utilized an oxiranyl anion strategy iteratively to construct the complex polycyclic architecture of gambierol, which includes 18 stereogenic centers and a partially conjugated triene side chain. The synthesis involved direct carbon-carbon bond formation on epoxides, sulfonyl-assisted 6-endo cyclization, and ring-expansion reactions to form seven-membered rings. Key steps included the coupling of oxiranyllithium with various triflates, ring-expansion using trimethylsilyldiazomethane, and selective reduction and functional group transformations. The final step involved a Stille coupling reaction to incorporate the triene side chain. The synthesized gambierol matched the previously reported spectroscopic and physical data, demonstrating the effectiveness of the new synthetic approach.

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