(3β,7R,16E)-16,17-Didehydro-9-hydroxy-17-methoxy-2-oxocorynoxan-16-carboxylic acid methyl ester

CAS No.
5171-42-6
Chemical Name:
(3β,7R,16E)-16,17-Didehydro-9-hydroxy-17-methoxy-2-oxocorynoxan-16-carboxylic acid methyl ester
Synonyms
Speciofoline;(3β,7R,16E)-16,17-Didehydro-9-hydroxy-17-methoxy-2-oxocorynoxan-16-carboxylic acid methyl ester;Spiro[3H-indole-3,1'(5'H)-indolizine]-7'-acetic acid, 6'-ethyl-1,2,2',3',6',7',8',8'a-octahydro-4-hydroxy-α-(methoxymethylene)-2-oxo-, methyl ester, (αE,1'R,6'S,7'S,8'aR)-
CBNumber:
CB92303278
Molecular Formula:
C22H28N2O5
Molecular Weight:
400.47
MDL Number:
MOL File:
5171-42-6.mol

(3β,7R,16E)-16,17-Didehydro-9-hydroxy-17-methoxy-2-oxocorynoxan-16-carboxylic acid methyl ester Properties

Melting point 202-4°C

(3β,7R,16E)-16,17-Didehydro-9-hydroxy-17-methoxy-2-oxocorynoxan-16-carboxylic acid methyl ester Chemical Properties,Uses,Production

Description

The leaves of Mitragyna speciosa Korth contain this alkaloid which crystallizes from EtOH in colourless needles. It is laevorotatory with [α]22D - 103° (c 2.0, CHCI3). The ultraviolet spectrum has absorption maxima at 223, 242 and 290 mJ.1. The alkaloid has been shown to be a stereoisomer of rotundifoline (q.v.).

References

Beckett, Lee, Tackie., Tetrahedron Lett., 1709 (1963)

(3β,7R,16E)-16,17-Didehydro-9-hydroxy-17-methoxy-2-oxocorynoxan-16-carboxylic acid methyl ester Preparation Products And Raw materials

Raw materials

Preparation Products

(3β,7R,16E)-16,17-Didehydro-9-hydroxy-17-methoxy-2-oxocorynoxan-16-carboxylic acid methyl ester Speciofoline Spiro[3H-indole-3,1'(5'H)-indolizine]-7'-acetic acid, 6'-ethyl-1,2,2',3',6',7',8',8'a-octahydro-4-hydroxy-α-(methoxymethylene)-2-oxo-, methyl ester, (αE,1'R,6'S,7'S,8'aR)- 5171-42-6