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

Bailey, Patrick D.; Beard, Mark A.; Cresswell, Mark; Dang, Hoa P.T.; Pathak, Ravindra B.; Phillips, Theresa R.; Price, Richard A.

Abstract

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.

• Journal Article Type: Article
• Acceptance Date: Jan 17, 2013
• Online Publication Date: Jan 25, 2013
• Publication Date: 2013-03
• Deposit Date: Jun 16, 2023
• Journal: Tetrahedron Letters
• Print ISSN: 0040-4039
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 54
• Issue: 13
• Pages: 1726-1729
• DOI: https://doi.org/10.1016/j.tetlet.2013.01.074
• Keywords: Organic Chemistry; Drug Discovery; Biochemistry