Work

Construction of the 4-Azafluorenone Core in a Single Operation and Synthesis of Onychine

Year: 2024

Type: article

Abstract: This study describes the synthesis of the 4-azafluorenone core in a single operation using readily available starting materials. Condensation of an amidrazone with ninhydrin intercepts an intermediate 1,2,4-triazine derivative, which engages norbornadiene in a merged [4 + 2]/bis-retro[4 + 2] sequence to deliver the azafluorenone core. The tricyclic core established in this manner was elaborated to onychine, the simplest natural product in the 4-azafluorenone alkaloid family.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.4c01298

Authors: Victoria A. Lehman, Yun Ma, Jonathan R. Scheerer

Institution: William & Mary

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: College of William and Mary, National Institute of General Medical Sciences