drimentine A

Base Information

• Chemical Name: drimentine A
• CAS No.: 204398-90-3
• Molecular Formula: C₃₂H₄₅N₃O₂
• Molecular Weight: 503.728
• Mol file: 204398-90-3.mol

Synonyms:

Chemical Property of drimentine A

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

DrimentineA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Drimentine A is a terpenylated diketopiperazine antibiotic originally isolated from Actinomycete bacteria. It is active against Gram-positive and Gram-negative bacteria, fungi, and yeast and has anthelmintic properties.
• Uses: Drimentine A belongs to a novel class of antibiotics, possessing a new terpenylated diketopiperazine structure, with antibiotic, antifungal and anthelmintic activity. The mode of action of drimentine A has received little attention to date. Drimentine A is a novel antibiotic with a terpenylated diketopiperazine structure.

Technology Process of drimentine A

There total 14 articles about drimentine A 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: 35.0%

C32H47N3O3 → drimentine A (204398-90-3) + C32H45N3O2 + C32H45N3O2

Guidance literature:

With thionyl chloride; triethylamine; In dichloromethane; at -90 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1002/anie.201303334

Reference yield:

C26H36N2O3 → drimentine A (204398-90-3) + C32H45N3O2 + C32H45N3O2

Guidance literature:

Multi-step reaction with 5 steps

1.1: 2,4,6-trimethyl-pyridine; HATU / dichloromethane / 5 h / 22 °C / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 2 h / 22 °C / Inert atmosphere

3.1: ammonium hydroxide / methanol / 0.17 h / 22 °C / Inert atmosphere

4.1: cerium(III) chloride / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere; Sonication

4.2: 1 h / 0 - 22 °C / Inert atmosphere

5.1: triethylamine; thionyl chloride / dichloromethane / 0.17 h / -90 °C / Inert atmosphere

With 2,4,6-trimethyl-pyridine; ammonium hydroxide; thionyl chloride; cerium(III) chloride; triethylamine; HATU; trifluoroacetic acid; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1002/anie.201303334

Reference yield:

C37H55N3O6 → drimentine A (204398-90-3) + C32H45N3O2 + C32H45N3O2

Guidance literature:

Multi-step reaction with 4 steps

1.1: trifluoroacetic acid / dichloromethane / 2 h / 22 °C / Inert atmosphere

2.1: ammonium hydroxide / methanol / 0.17 h / 22 °C / Inert atmosphere

3.1: cerium(III) chloride / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere; Sonication

3.2: 1 h / 0 - 22 °C / Inert atmosphere

4.1: triethylamine; thionyl chloride / dichloromethane / 0.17 h / -90 °C / Inert atmosphere

With ammonium hydroxide; thionyl chloride; cerium(III) chloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1002/anie.201303334

upstream raw materials:

(3aR)-(+)-sclareolide

(1R,2R,4aS,8aS)-1-(iodoethyl)-2,5,5,8a-tetramethyldecahydronaphthalen-2-yl formate

(4aS,8aS)-3,4,4aα,5,6,7,8,8aβ-octahydro-5,5,8aβ-trimethyl-1-methylidene-2(1H)-naphthalenone

tert-butyl (+)-(S)-3-[2-(tert-butoxycarbonylamino)-3-methoxy-3-oxopropyl]-1H-indole-1-carboxylate

Refernces