Total synthesis of phenanthroindolizidine alkaloids through an amidyl radical cascade/rearrangement reaction

Guifang Han; Yuxiu Liu; Qingmin Wang

doi:10.1021/ol4025925

Total synthesis of phenanthroindolizidine alkaloids through an amidyl radical cascade/rearrangement reaction

Org Lett. 2013 Oct 18;15(20):5334-7. doi: 10.1021/ol4025925. Epub 2013 Oct 9.

Authors

Guifang Han¹, Yuxiu Liu, Qingmin Wang

Affiliation

¹ State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, China.

PMID: 24107089
DOI: 10.1021/ol4025925

Abstract

A short and general synthesis of the phenanthroindolizidine alkaloids is reported, featuring an unusual amidyl radical 5-exo/5-exo/rearrangement cascade of a xanthate precursor. Second, using an amidyl radical 5-exo/6-endo cascade to synthesize a phenanthroindolizidine alkaloid exclusively has been developed through a small structural modification.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry
Amides / chemistry*
Free Radicals / chemistry
Indolizines / chemical synthesis*
Indolizines / chemistry
Molecular Structure
Phenanthrolines / chemical synthesis*
Phenanthrolines / chemistry
Stereoisomerism

Substances

Alkaloids
Amides
Free Radicals
Indolizines
Phenanthrolines
phenanthroindolizidine