dvances Towards the Synthesis of Aporphine Alkaloids: C-Ring Formation via Approaches Based on One- and Two-Bond Disconnection

Author(s)

Silva, Tamiris R. C. ^[1] ; Rita, Bruno H. ^[1] ; Raminelli, Cristiano ^[1]

Affiliation

^[1] Univ Fed Sao Paulo, Inst Ciencias Ambientais Quim & Farmaceut, Rua Prof Artur Riedel 275, BR-09972270 Diadema, SP - Brazil

• Document type: Review article
• Source: CHEMICAL RECORD; v. 22, n. 2 NOV 2021.
• Web of Science Citations: 0

Abstract

Aporphine compounds constitute a class of substances with important pharmacological properties, including anticancer, antiviral, anti-HIV, anti-inflammatory, and leishmanicidal activities. Consequently, several strategies to obtain the aporphine core have been reported. Herein this review, we provide an overview of two relevant approaches used to construct the C-ring in the synthetic routes developed. The first approach, which is based on a one-bond disconnection, allows C-ring formation using a 1-benzyl-1,2,3,4-tetrahydroisoquinoline intermediate (mainly) employing cyclization reactions catalyzed by metals or promoted by light. The second approach, which is derived from a two-bond disconnection, leads to C-ring formation via a sequence of reactions starting with {[}4+2] cycloadditions. Through these approaches, aporphinoids with a diverse range of substitution patterns and biological activities can be synthesized. (AU)

• FAPESP's process: 20/12530-8 - 2-(Trimethylsilyl)aryl trifluoromethanesulfonates as aryne precursors aiming to the preparation of functionalized (hetero)aromatic compounds and syntheses of bioactive natural products
• Grantee: Cristiano Raminelli
• Support Opportunities: Regular Research Grants