Work

Bioinspired Synthesis of (−)‐Hunterine A: Deciphering the Key Step in the Biogenetic Pathway

Year: 2024

Type: article

Abstract: A concise, bioinspired, and enantioselective synthesis of (-)-hunterine A, an odd 6/7/6/6/5 pentacyclic natural product, is described. The key step in the synthesis of this complex structure is an interim-template directed 6-exo selective epoxide ring-opening reaction, which is interwoven with a hydrolysis step of the indolenine hemiaminal template to create the unusual 7-membered azepine bridge motif. Our work not only refines the previously proposed biogenetic pathway, but also reveals the possible stereochemical prerequisite of the unique skeletal rearrangement, which provides a vantage point for understanding how (-)-hunterine A is likely to be generated in nature.

Source: Chemistry - A European Journal

DOI: 10.1002/chem.202404501

Authors: Bálint Zsigulics, Péter Angyal, Bence Balázs Mészáros, János Daru, Szilárd Varga, Tibor Soós

Institutions: Eötvös Loránd University, Institute of Organic Chemistry, HUN-REN Research Centre for Natural Sciences

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: Nemzeti Kutatási Fejlesztési és Innovációs Hivatal, Servier, Nemzeti Kutatási, Fejlesztési és Innovaciós Alap