(5β,12S,19β)-2,3-Didehydro-7α-ethyl-8,20,21-trinoraspidospermidine-3-carboxylic acid methyl ester

Base Information

Chemical Name:(5β,12S,19β)-2,3-Didehydro-7α-ethyl-8,20,21-trinoraspidospermidine-3-carboxylic acid methyl ester
CAS No.:59871-84-0
Molecular Formula:C20H24N2O2
Molecular Weight:324.42
Hs Code.:
Mol file:59871-84-0.mol

Synonyms:

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Chemical Property of (5β,12S,19β)-2,3-Didehydro-7α-ethyl-8,20,21-trinoraspidospermidine-3-carboxylic acid methyl ester

Chemical Property:

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Description A recent reinvestigation of the alkaloids present in the leaves of Tabernanthe iboga and T. subsessilis has resulted in the isolation of two new bases, ibophyllidine and iboxyphylline (q.v.). Ibophyllidine has been obtained as a non-crystallizable solid having no definite melting point. It is dextrorotatory with a specific rotation of [cd D + 1340 (c 1.0, CHCI3) and gives an ultraviolet spectrum in EtOH consisting of absorption maxima at 227,302 and 333 nm. The structure has been deduced primarily from a study of the ultraviolet and NMR spectra.

Technology Process of (5β,12S,19β)-2,3-Didehydro-7α-ethyl-8,20,21-trinoraspidospermidine-3-carboxylic acid methyl ester

There total 16 articles about (5β,12S,19β)-2,3-Didehydro-7α-ethyl-8,20,21-trinoraspidospermidine-3-carboxylic acid methyl ester 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: 51.0%

: 1397506-11-4
C₂₀H₂₆N₂O₂

: 59871-84-0
(+)-ibophyllidine

Guidance literature:: With Dess-Martin periodane; In dichloromethane;
DOI:10.1039/c2sc20468a

Reference yield:

: 1397505-87-1
C₂₂H₂₇ClN₂O₄

: 59871-84-0
(+)-ibophyllidine

Guidance literature:: Multi-step reaction with 8 steps

1: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C

2: silica gel / toluene / Reflux

3: sodium iodide / acetone / Reflux

4: triethylamine; silver trifluoromethanesulfonate / toluene / 0 - 20 °C

5: trimethylphosphane / benzene; methanol

6: Lawessons reagent / benzene / Reflux

7: hydrogen / tetrahydrofuran / 10343.2 Torr

8: Dess-Martin periodane / dichloromethane

With Lawessons reagent; hydrogen; silver trifluoromethanesulfonate; sodium hexamethyldisilazane; silica gel; Dess-Martin periodane; triethylamine; sodium iodide; trimethylphosphane; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; benzene; 1: |Horner-Wadsworth-Emmons Olefination / 3: |Finkelstein Reaction / 5: |Baylis-Hillman Reaction;
DOI:10.1039/c2sc20468a

Reference yield:

: C₂₅H₃₁ClN₂O₅

: 59871-84-0
(+)-ibophyllidine

Guidance literature:: Multi-step reaction with 7 steps

1: silica gel / toluene / Reflux

2: sodium iodide / acetone / Reflux

3: triethylamine; silver trifluoromethanesulfonate / toluene / 0 - 20 °C

4: trimethylphosphane / benzene; methanol

5: Lawessons reagent / benzene / Reflux

6: hydrogen / tetrahydrofuran / 10343.2 Torr

7: Dess-Martin periodane / dichloromethane

With Lawessons reagent; hydrogen; silver trifluoromethanesulfonate; silica gel; Dess-Martin periodane; triethylamine; sodium iodide; trimethylphosphane; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; benzene; 2: |Finkelstein Reaction / 4: |Baylis-Hillman Reaction;
DOI:10.1039/c2sc20468a