Myrrhine

Base Information

• Chemical Name: Myrrhine
• CAS No.: 58207-39-9
• Molecular Formula: C₁₃H₂₃N
• Molecular Weight: 193.332
• Mol file: 58207-39-9.mol

Synonyms:6a-epi-Precoccinelline; Myrrhine

Chemical Property of Myrrhine

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: This alkaloid occurs in Myrrha octodecimguttata. The structure has been established by correlation with that of coccinelline.

Technology Process of Myrrhine

There total 54 articles about Myrrhine 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: 37.0%

(3aSR,9aSR)-2-methylene-dodecahydro-pyrido[2,1,6-de]quinolizine → (+/-)-epi-hippodamine (38211-56-2,53955-49-0,53990-36-6,58207-39-9,59685-36-8,72362-39-1,138812-41-6) + (+/-)-hippodamine (59685-36-8)

Guidance literature:

(3aSR,9aSR)-2-methylene-dodecahydro-pyrido[2,1,6-de]quinolizine; With mesitylene sulfonic acid; In tetrahydrofuran; at 20 ℃; for 1h;

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; for 48h; normal pressure;

DOI:10.1039/b413052a

Reference yield:

2-[1-(4,5-dihydroxy-pentyl)-5,6-dihydroxy-hexyl]-isoindole-1,3-dione → (+/-)-epi-hippodamine (38211-56-2,53955-49-0,53990-36-6,58207-39-9,59685-36-8,72362-39-1,138812-41-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium periodate / tetrahydrofuran; 2-methyl-propan-2-ol / 20 h / 20 °C

2.1: NaH / tetrahydrofuran / 2 h / 20 °C

2.2: 9.76 g / tetrahydrofuran / 48 h / 20 °C

3.1: 66.9 percent / aq. NaBH₄ / propan-2-ol / 24 h / 20 °C

4.1: 4.38 g / glacial acetic acid / propan-2-ol; acetone / 24 h / Heating

5.1: t-BuOK; Li / benzene / 19 h / Heating

5.2: HCl / CHCl₃; diethyl ether / 1 h / 20 °C

5.3: 0.764 g / aq. LiCl / dimethylformamide / 4 h / Heating

6.1: 61.2 percent / toluene; diethyl ether / 5 h / 0 °C

7.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

7.2: tetrahydrofuran; hexane / 3 h / -78 - 20 °C

7.3: tetrahydrofuran; hexane / 20 °C

8.1: tri-n-butyltin hydride; AIBN / toluene / 4 h / Heating

With sodium tetrahydroborate; sodium periodate; n-butyllithium; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; tri-n-butyl-tin hydride; lithium; sodium hydride; acetic acid; In tetrahydrofuran; diethyl ether; hexane; isopropyl alcohol; acetone; toluene; tert-butyl alcohol; benzene; 2.1: Wadsworth-Emmons reaction / 5.1: Dieckmann condensation;

DOI:10.1039/b413052a

Reference yield:

7-(2'-hydroxymethyl-benzoylamino)-trideca-2,11-dienedioic acid diethyl ester (835617-24-8) → (+/-)-epi-hippodamine (38211-56-2,53955-49-0,53990-36-6,58207-39-9,59685-36-8,72362-39-1,138812-41-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 4.38 g / glacial acetic acid / propan-2-ol; acetone / 24 h / Heating

2.1: t-BuOK; Li / benzene / 19 h / Heating

2.2: HCl / CHCl₃; diethyl ether / 1 h / 20 °C

2.3: 0.764 g / aq. LiCl / dimethylformamide / 4 h / Heating

3.1: 61.2 percent / toluene; diethyl ether / 5 h / 0 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

4.2: tetrahydrofuran; hexane / 3 h / -78 - 20 °C

4.3: tetrahydrofuran; hexane / 20 °C

5.1: tri-n-butyltin hydride; AIBN / toluene / 4 h / Heating

With n-butyllithium; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; tri-n-butyl-tin hydride; lithium; acetic acid; In tetrahydrofuran; diethyl ether; hexane; isopropyl alcohol; acetone; toluene; benzene; 2.1: Dieckmann condensation;

DOI:10.1039/b413052a

upstream raw materials:

(2α,3aβ,6aβ,9aβ)-dodecahydro-2-(hydroxymethyl)pyrido<2,1,6-de>quinolizine, methanesulfonate ester

(3aα,6aα,9aα)-(+/-)-1,2,3,3a,4,5,6,6a,7,9a-decahydropyrido<2,1,6-de>quinolizine-8-carboxaldehyde

(3aα,6aα,9aα)-(+/-)-2-<(n-butylthio)methylene>decahydropyrido<2,1,6-de>quinolizin-1(2H)-one

(3aα,6aα,9aα)-(+/-)-decahydropyrido<2,1,6-de>quinolizin-1(2H)-one

Downstream raw materials:

myrrhine N-oxide

Refernces

• 1、 Diaz-Gavilan, Monica,Galloway, Warren R. J. D.,O'Connell, Kieron M. G.,Hodkingson, James T.,Spring, David R.. "Diversity-oriented synthesis of bicyclic and tricyclic alkaloids". supporting information; experimental part. p. 776 - 778. Retrieved 2010/06/12.
• 2、 Rejzek, Martin,Stockman, Robert A.,Hughes, David L.. "Combining two-directional synthesis and tandem reactions:? an efficient strategy for the total syntheses of (±)-hippodamine and (±)-epi-hippodamine". . p. 73 - 83. Retrieved 2007/10/03.