(+)-Dendrillolide C

Base Information

• Chemical Name: (+)-Dendrillolide C
• CAS No.: 91158-70-2
• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.441
• Mol file: 91158-70-2.mol

Synonyms:(3aR,6aR)-4-((1R,3aR,8aS)-1,4,4-Trimethyl-8-methylene-decahydro-azulen-1-yl)-3a,6a-dihydro-3H-furo[2,3-b]furan-2-one;

Chemical Property of (+)-Dendrillolide C

Chemical Property:

• PSA: 35.53000
• LogP: 4.58850

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (+)-Dendrillolide C

There total 15 articles about (+)-Dendrillolide C 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: 77.0%

(+)-cheloviolene B → (+)-dendrillolide C (91158-70-2)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In toluene; at 0 - 90 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jacs.7b04265

Reference yield:

fenchone (4695-62-9,126-21-6) → (+)-dendrillolide C (91158-70-2)

Guidance literature:

Multi-step reaction with 15 steps

1.1: hydroxylamine hydrochloride; sodium acetate / ethanol; water / 36 h / Reflux

2.1: sulfuric acid / water / 0.5 h / 120 °C

3.1: diisobutylaluminium hydride / dichloromethane / -78 - 23 °C / Inert atmosphere

4.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / 23 °C / Inert atmosphere

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / -10 °C

6.1: 2,2,6,6-tetramethylpiperidine hydrobromide; n-butyllithium / tetrahydrofuran / 0 - 60 °C / Inert atmosphere

7.1: hydrogen / methanol; acetic acid / 5 h / 23 - 70 °C / 38002.6 Torr

8.1: 3-chloro-benzenecarboperoxoic acid; potassium carbonate / N,N-dimethyl-formamide / 12 h / 120 °C / Inert atmosphere

9.1: tetrahydrofuran / 6 h / 0 - 23 °C / Inert atmosphere

10.1: Ir[dF(CF₃)ppy]₂(dtbpy)PF₆; dipotassium hydrogenphosphate / tetrahydrofuran; water / 18 h / 23 - 60 °C / Inert atmosphere; Irradiation

10.2: 4 h / 60 °C / Inert atmosphere; Irradiation

11.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

11.2: 1 h / -78 °C / Inert atmosphere

12.1: diisobutylaluminium hydride / toluene / 1 h / -78 °C / Inert atmosphere

13.1: pyridinium chlorochromate / dichloromethane / 9 h / 23 °C

14.1: hydrogenchloride; water / tetrahydrofuran / 72 h / 23 °C

15.1: triethylamine; methanesulfonyl chloride / toluene / 1 h / 0 - 90 °C / Inert atmosphere

With hydrogenchloride; dipotassium hydrogenphosphate; n-butyllithium; sulfuric acid; Ir[dF(CF₃)ppy]₂(dtbpy)PF₆; hydroxylamine hydrochloride; water; hydrogen; sodium acetate; 2,2,6,6-tetramethylpiperidine hydrobromide; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; toluene; 4.1: |Wittig Olefination / 7.1: |Eschweiler-Clarke Methylation / 8.1: |Cope Elimination;

DOI:10.1021/jacs.7b04265

Reference yield:

fenchone oxime (40514-83-8) → (+)-dendrillolide C (91158-70-2)

Guidance literature:

Multi-step reaction with 14 steps

1.1: sulfuric acid / water / 0.5 h / 120 °C

2.1: diisobutylaluminium hydride / dichloromethane / -78 - 23 °C / Inert atmosphere

3.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / 23 °C / Inert atmosphere

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / -10 °C

5.1: 2,2,6,6-tetramethylpiperidine hydrobromide; n-butyllithium / tetrahydrofuran / 0 - 60 °C / Inert atmosphere

6.1: hydrogen / methanol; acetic acid / 5 h / 23 - 70 °C / 38002.6 Torr

7.1: 3-chloro-benzenecarboperoxoic acid; potassium carbonate / N,N-dimethyl-formamide / 12 h / 120 °C / Inert atmosphere

8.1: tetrahydrofuran / 6 h / 0 - 23 °C / Inert atmosphere

9.1: Ir[dF(CF₃)ppy]₂(dtbpy)PF₆; dipotassium hydrogenphosphate / tetrahydrofuran; water / 18 h / 23 - 60 °C / Inert atmosphere; Irradiation

9.2: 4 h / 60 °C / Inert atmosphere; Irradiation

10.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

10.2: 1 h / -78 °C / Inert atmosphere

11.1: diisobutylaluminium hydride / toluene / 1 h / -78 °C / Inert atmosphere

12.1: pyridinium chlorochromate / dichloromethane / 9 h / 23 °C

13.1: hydrogenchloride; water / tetrahydrofuran / 72 h / 23 °C

14.1: triethylamine; methanesulfonyl chloride / toluene / 1 h / 0 - 90 °C / Inert atmosphere

With hydrogenchloride; dipotassium hydrogenphosphate; n-butyllithium; sulfuric acid; Ir[dF(CF₃)ppy]₂(dtbpy)PF₆; water; hydrogen; 2,2,6,6-tetramethylpiperidine hydrobromide; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; toluene; 3.1: |Wittig Olefination / 6.1: |Eschweiler-Clarke Methylation / 7.1: |Cope Elimination;

DOI:10.1021/jacs.7b04265

upstream raw materials:

fenchone

fenchone oxime

2-Methyl-2-<(1R)-3-methyl-2-cyclopentenyl>propannitril

Refernces