Work

Synthesis of Demissidine by a Ring Fragmentation 1,3-Dipolar Cycloaddition Approach

Year: 2013

Type: article

Abstract: A synthesis of the steroidal alkaloid demissidine from epiandrosterone is reported. A ring fragmentation reaction that efficiently ruptured the D-ring of a diazo ester derivative of epiandrosterone to provide an aldehyde tethered ynoate product was key to this sequence. Incorporation of the indolizidine framework was achieved by an azomethine ylide 1,3-dipolar cycloaddition.

Source: Organic Letters

DOI: 10.1021/ol4004993

Authors: Zhe Zhang, Geoffrey M. Giampa, Cristian Draghici, Qiufeng Huang, Matthias Brewer

Institution: University of Vermont

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: G1497838195, G2949381749, G4202910764