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(5bR)-5,5bα,6,6aβ,10,11,16,16b,16cα,17,19,20-Dodecahydro-16bβ-methylbisindolo[2',3':3,4]pyrido[2,1-a:2',1'-g][2,7]naphthyridine-7-carboxylic acid methyl ester

(5bR)-5,5bα,6,6aβ,10,11,16,16b,16cα,17,19,20-Dodecahydro-16bβ-methylbisindolo[2',3':3,4]pyrido[2,1-a:2',1'-g][2,7]naphthyridine-7-carboxylic acid methyl ester Structure
(5bR)-5,5bα,6,6aβ,10,11,16,16b,16cα,17,19,20-Dodecahydro-16bβ-methylbisindolo[2',3':3,4]pyrido[2,1-a:2',1'-g][2,7]naphthyridine-7-carboxylic acid methyl ester structure
CAS No.
27802-03-5
Chemical Name:
(5bR)-5,5bα,6,6aβ,10,11,16,16b,16cα,17,19,20-Dodecahydro-16bβ-methylbisindolo[2',3':3,4]pyrido[2,1-a:2',1'-g][2,7]naphthyridine-7-carboxylic acid methyl ester
Synonyms
Roxburghine;Roxburghine D;(5bR)-5,5bα,6,6aβ,10,11,16,16b,16cα,17,19,20-Dodecahydro-16bβ-methylbisindolo[2',3':3,4]pyrido[2,1-a:2',1'-g][2,7]naphthyridine-7-carboxylic acid methyl ester;Diindolo[2',3':3,4]pyrido[2,1-a:2',1'-g][2,7]naphthyridine-7-carboxylic acid, 5,5b,6,6a,10,11,16,16b,16c,17,19,20-dodecahydro-16b-methyl-, methyl ester, (5bR,6aS,16bS,16cR)-
CBNumber:
CB42221968
Molecular Formula:
C31H32N4O2
Molecular Weight:
492.61
MDL Number:
MOL File:
27802-03-5.mol
Request For Quotation

(5bR)-5,5bα,6,6aβ,10,11,16,16b,16cα,17,19,20-Dodecahydro-16bβ-methylbisindolo[2',3':3,4]pyrido[2,1-a:2',1'-g][2,7]naphthyridine-7-carboxylic acid methyl ester Properties

Melting point 197-200°C

(5bR)-5,5bα,6,6aβ,10,11,16,16b,16cα,17,19,20-Dodecahydro-16bβ-methylbisindolo[2',3':3,4]pyrido[2,1-a:2',1'-g][2,7]naphthyridine-7-carboxylic acid methyl ester Chemical Properties,Uses,Production

Description

This alkaloid also occurs in the leaves of Uncaria gambier and forms colourless crystals from MeOH. It is, unlike the remaining alkaloids, dextrorotatory with [α]20D + 160° (MeOH) but the ultraviolet spectrum in EtOH is almost identical with those of the preceding bases, having absorption maxima at 226 and 292 ITIJ1 with a shoulder at 287 mfl. On catalytic hydrogenation it gives the dihydro derivative, m.p. 225-230°C.

References

Merlini et al., Tetrahedron, 26,2259 (1970)

(5bR)-5,5bα,6,6aβ,10,11,16,16b,16cα,17,19,20-Dodecahydro-16bβ-methylbisindolo[2',3':3,4]pyrido[2,1-a:2',1'-g][2,7]naphthyridine-7-carboxylic acid methyl ester Preparation Products And Raw materials

Raw materials

Preparation Products

(5bR)-5,5bα,6,6aβ,10,11,16,16b,16cα,17,19,20-Dodecahydro-16bβ-methylbisindolo[2',3':3,4]pyrido[2,1-a:2',1'-g][2,7]naphthyridine-7-carboxylic acid methyl ester Roxburghine Roxburghine D Diindolo[2',3':3,4]pyrido[2,1-a:2',1'-g][2,7]naphthyridine-7-carboxylic acid, 5,5b,6,6a,10,11,16,16b,16c,17,19,20-dodecahydro-16b-methyl-, methyl ester, (5bR,6aS,16bS,16cR)- 27802-03-5