4-[(4E,8E)-15-Hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-1,3-thiazolidin-2-one

Base Information

• Chemical Name: 4-[(4E,8E)-15-Hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-1,3-thiazolidin-2-one
• CAS No.: 76343-94-7
• Molecular Formula: C₂₀H₂₉NO₅S
• Molecular Weight: 395.52
• NSC Number: 339663
• Mol file: 76343-94-7.mol

Synonyms:4-[(4E,8E)-15-Hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-1,3-thiazolidin-2-one;76343-94-7;NSC339663

Chemical Property of 4-[(4E,8E)-15-Hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-1,3-thiazolidin-2-one

Chemical Property:

• Appearance/Colour: Off white to yellow lyophilized solid
• PSA: 110.16000
• Density: 1.178 g/cm³
• LogP: 3.63220
• Storage Temp.: −20°C
• Solubility.: DMSO: soluble
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 395.17664420
• Heavy Atom Count: 27
• Complexity: 634

Purity/Quality:

99% ^*data from raw suppliers

Latrunculin B ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2CC(CC(O2)(C3CSC(=O)N3)O)OC(=O)C=C(CCC=C1)C
• Isomeric SMILES: CC\1CCC2CC(CC(O2)(C3CSC(=O)N3)O)OC(=O)/C=C(/CC/C=C1)\C
• General Description: Latrunculin B is a structurally complex macrolide toxin originally isolated from the Red Sea sponge *Latrunculia magnifica*. It is known for its ability to disrupt actin polymerization, making it a valuable tool for studying cytoskeletal dynamics. The compound features a 2-thiazolidinone ring and a bicyclic core, with key stereochemical elements critical to its biological activity. Its synthesis involves convergent strategies, including aldol reactions and macrolide cyclization, highlighting its intricate architecture. Latrunculin B's potent bioactivity and unique structure have made it a subject of interest in both chemical synthesis and cell biology research.

Technology Process of 4-[(4E,8E)-15-Hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-1,3-thiazolidin-2-one

There total 40 articles about 4-[(4E,8E)-15-Hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-1,3-thiazolidin-2-one 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: 78.0%

6,7-(Z)-N-PMB-15-OMe-Latrunculin B (101915-87-1) → latrunculin B (76343-94-7)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile;

DOI:10.1002/anie.200352413

Reference yield: 59.0%

6,7-(Z)-15-OMe-Latrunculin B (105917-28-0) → latrunculin B (76343-94-7)

Guidance literature:

With water; acetic acid; In tetrahydrofuran; at 60 ℃; for 2h;

DOI:10.1021/ja00034a036

Reference yield:

(3R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-non-7-ynal (646994-44-7) → latrunculin B (76343-94-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 75 percent / Ba(OH)2*8H₂O / tetrahydrofuran; H₂O / 3 h

2: 57 percent / aq. HCl / tetrahydrofuran / 20 °C

3: 92 percent / camphor-10-sulfonic acid / 20 °C

4: pyridine / CH₂Cl₂ / 1 h / -20 °C

5: 45 mg / [15]crown-5 ether / tetrahydrofuran / 20 °C

6: 70 percent / Mo[N-(tBu)(3,5-dimethylphenyl)]3 / toluene / 20 h / 80 °C

7: 100 percent / hydrogen / Lindlar / CH₂Cl₂

8: 78 percent / aq. cerium ammonium nitrate / acetonitrile / 3 h

With pyridine; hydrogenchloride; barium dihydroxide; ammonium cerium(IV) nitrate; hydrogen; Lindlar's catalyst; 15-crown-5; tris(N-tert-butyl-3,5-dimethylanilino)molybdenum(III); camphor-10-sulfonic acid; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile;

DOI:10.1002/chem.200601135

upstream raw materials:

6,7-(Z)-15-OMe-Latrunculin B

6,7-(Z)-N-PMB-15-OMe-Latrunculin B

dimethyl 2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-2-oxoethyl-phosphonate

(R)-4-[(E)-(5R,8S)-5-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-undec-2-en-9-ynoyl]-3-(4-methoxy-benzyl)-thiazolidin-2-one

Downstream raw materials:

latrunculin-C

Refernces

Total synthesis of the latrunculins

10.1021/ja00034a036

The research details the total synthesis of latrunculins A and B, two architecturally novel toxins isolated from the Red Sea sponge Latrunculia magnifica. The study presents highly convergent and stereocontrolled routes to achieve these syntheses, with the longest linear sequences being 16 and 12 steps, respectively. Key chemicals and strategies involved in the synthesis include the aldol reaction of aldehyde (-)-12 with methyl ketone (-)-13, an acid-catalyzed reorganization-equilibration of ortho ester (-)-11, and a Mitsunobu macrolide cyclization. The synthesis also involves the preparation of various intermediates such as aldehyde (-)-12 derived from (f)-2-allylcyclopentanone and (+)-(R,R)-2,3-butanediol, and ketone (-)-13 derived from L-cysteine ethyl ester. The research highlights the challenges and solutions in achieving the correct stereochemistry and configuration of the target compounds, showcasing the importance of protecting group strategies and selective reagents like lithium bis(trimethylsilyl)amide and dibutylboron triflate. The successful synthesis of latrunculins A and B provides valuable insights into the structure and function of these toxins, which have significant biological profiles and potential applications in studying actin microfilament structure and function.