(4aR,7S)-4-Acetyl-6α,9α-epimino-4aβ,5,6,8,9,9aβ-hexahydro-1'-methylspiro[cyclohepta[c]pyran-7(1H),3'-[3H]indol]-2'(1'H)-one

Base Information

• Chemical Name: (4aR,7S)-4-Acetyl-6α,9α-epimino-4aβ,5,6,8,9,9aβ-hexahydro-1'-methylspiro[cyclohepta[c]pyran-7(1H),3'-[3H]indol]-2'(1'H)-one
• CAS No.: 35804-91-2
• Molecular Formula: C20H22N2O3
• Molecular Weight: 338.40028
• Mol file: 35804-91-2.mol

Synonyms:alstonal;alstonisine;

Chemical Property of (4aR,7S)-4-Acetyl-6α,9α-epimino-4aβ,5,6,8,9,9aβ-hexahydro-1'-methylspiro[cyclohepta[c]pyran-7(1H),3'-[3H]indol]-2'(1'H)-one

Chemical Property:

• PSA: 58.64000
• LogP: 2.16430

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (4aR,7S)-4-Acetyl-6α,9α-epimino-4aβ,5,6,8,9,9aβ-hexahydro-1'-methylspiro[cyclohepta[c]pyran-7(1H),3'-[3H]indol]-2'(1'H)-one

There total 26 articles about (4aR,7S)-4-Acetyl-6α,9α-epimino-4aβ,5,6,8,9,9aβ-hexahydro-1'-methylspiro[cyclohepta[c]pyran-7(1H),3'-[3H]indol]-2'(1'H)-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: 70.0%

(+)-7R-isoalstonisine → alstonisine (35804-91-2)

Guidance literature:

With pyridine; In dichloromethane; at 100 - 110 ℃; for 60h; Inert atmosphere; Sealed tube;

DOI:10.1002/chem.201703572

Reference yield:

C21H26N2O4 → alstonisine (35804-91-2)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 2h;

DOI:10.1021/ol020170b

Reference yield:

(6S,10S)-5-methyl-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde (219583-98-9) → alstonisine (35804-91-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: N-phenylselenophthalimide; p-toluenesulfonic acid / CH₂Cl₂; methanol

1.2: 90 percent / sodium metaperiodate / tetrahydrofuran; H₂O / 10 h / 0 °C

2.1: BH₃*THF / 14 h / 0 °C

2.2: 85 percent / hydrogen peroxide / tetrahydrofuran

3.1: 80 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 1.5 h

4.1: osmium tetraoxide; pyridine / tetrahydrofuran / 72 h / 20 °C

4.2: 81 percent / sodium hydrogen sulfite / tetrahydrofuran; H₂O

5.1: hydrogen / Pd(OH)2/C / ethanol / 5 h / 20 °C

6.1: sodium hydroxide / methanol / 2 h / 20 °C

With pyridine; sodium hydroxide; osmium(VIII) oxide; borane-THF; oxalyl dichloride; N-phenylselanylphthalimide; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; 4.1: Swern oxidation;

DOI:10.1021/ol020170b

upstream raw materials:

(6S,10S)-5-methyl-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde

C₂₇H₃₀N₂O

C₂₈H₃₂N₂O₂

C₂₈H₃₂N₂O₃

Refernces

• 1、 Yang, Jie,Wearing, Xiangyu Z.,Le Quesne, Philip W.,Deschamps, Jeffrey R.,Cook, James M.. "Enantiospecific synthesis of (+)-alstonisine via a stereospecific osmylation process". experimental part. p. 1431 - 1440. Retrieved 2009/04/07.