Work

Formal Synthesis of Aspidosperma Alkaloids via the Intramolecular [3 + 2] Cycloaddition of 2-Azapentdienyllithiums

Year: 2006

Type: article

Abstract: [reaction: see text] A formal synthesis of the Aspidosperma alkaloids aspidospermidine, aspidospermine, and quebrachamine is reported through an efficient preparation of Stork's penultimate intermediate. The key step of the sequence involved an intramolecular [3 + 2] cycloaddition of the 2-azapentadienyllithium 21 formed in situ from the corresponding imine 1, which after N-alkylation of the resulting cycloadduct provided 2 in excellent yield. The synthesis represents a new disconnection of the classical tricyclic ketone used for appendage of the requisite indole.

Source: Organic Letters

DOI: 10.1021/ol0602506

Authors: William H. Pearson, Aaron Aponick

Institution: University of Michigan

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: G5998031071, ALKALOID SYNTHESIS VIA (3+2) CYCLOADDITIONS