15,23-Dideoxy-19,23-epoxy-6β-hydroxyajaconine

CAS No.
21040-66-4
Chemical Name:
15,23-Dideoxy-19,23-epoxy-6β-hydroxyajaconine
Synonyms
Spiradine G;15,23-Dideoxy-19,23-epoxy-6β-hydroxyajaconine;12aH,14H-3,14a-Ethano-14,4b,8-ethanylylidene-1H,5H-[2]benzopyrano[4,3-g]oxazolo[3,2-a]azocin-17-ol, decahydro-8-methyl-2-methylene-, (3S,4aR,4bR,8R,8aR,12aS,14S,14aR,17S,18R)- (9CI)
CBNumber:
CB22428956
Molecular Formula:
C22H31NO3
Molecular Weight:
357.49
MDL Number:
MOL File:
21040-66-4.mol

15,23-Dideoxy-19,23-epoxy-6β-hydroxyajaconine Properties

Melting point 168-l700 C

15,23-Dideoxy-19,23-epoxy-6β-hydroxyajaconine Chemical Properties,Uses,Production

Description

A sixth alkaloid found in Spiraea japonica L. fil., the base is laevorotatory with [α]D - 137° (c 1.16, MeOH). Reduction with NaBH4 gives a triol while oxida_x0002_tion with chromic acid in pyridine forms a monoketone, m.p. IS8-l60°C. The presence of an exocyclic methylene group is confirmed by catalytic reduction and subsequent oxidation with KMn04 to give a ketone.

References

Toda, Hirata., Tetrahedron Lett., 5565 (1968)

15,23-Dideoxy-19,23-epoxy-6β-hydroxyajaconine Preparation Products And Raw materials

Raw materials

Preparation Products

15,23-Dideoxy-19,23-epoxy-6β-hydroxyajaconine Spiradine G 12aH,14H-3,14a-Ethano-14,4b,8-ethanylylidene-1H,5H-[2]benzopyrano[4,3-g]oxazolo[3,2-a]azocin-17-ol, decahydro-8-methyl-2-methylene-, (3S,4aR,4bR,8R,8aR,12aS,14S,14aR,17S,18R)- (9CI) 21040-66-4