Stereoselectivity and conformational control in the synthesis of ajmaline and epi-ajmaline alkaloids

Appropriate choice of protecting group P and reducing agent allows access to either the natural or epi series of ajmaline alkaloids. Careful choice of the N-protecting group provides crucial conformational control, allowing ring-closure to the indole 3-position in the late stages of the synthesis of...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2013-03, Vol.54 (13), p.1726-1729
Main Authors: Bailey, Patrick D., Beard, Mark A., Cresswell, Mark, Dang, Hoa P.T., Pathak, Ravindra B., Phillips, Theresa R., Price, Richard A.
Format: Article
Language:English
Subjects:
Access control
Ajmaline
Alkaloids
Indole alkaloids
Indoles
Reducing agents
Stereoselective synthesis
Stereoselectivity
Synthesis (chemistry)
Tetrahedrons
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Appropriate choice of protecting group P and reducing agent allows access to either the natural or epi series of ajmaline alkaloids. Careful choice of the N-protecting group provides crucial conformational control, allowing ring-closure to the indole 3-position in the late stages of the synthesis of ajmaline alkaloids; the choice of protecting group and reducing agent can also provide access to either the natural or epi configuration at the indole 2-position.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.01.074