Bioinspired Synthesis of (-)-Hunterine A: Deciphering the Key Step in the Biogenetic Pathway.

Autor: Zsigulics B; Research Centre for Natural Sciences: Termeszettudomanyi Kutatokozpont, Institute of Organic Chemistry, HUNGARY., Angyal P; Research Centre for Natural Sciences: Termeszettudomanyi Kutatokozpont, Institute of Organic Chemistry, HUNGARY., Mészáros BB; Research Centre for Natural Sciences: Termeszettudomanyi Kutatokozpont, Institute of Organic Chemistry, HUNGARY., Daru J; Eotvos Lorand University: Eotvos Lorand Tudomanyegyetem, Institute of Chemistry, HUNGARY., Varga S; Research Centre for Natural Sciences: Termeszettudomanyi Kutatokozpont, Institute of Organic Chemistry, HUNGARY., Soós T; Research Centre for Natural Sciences: Termeszettudomanyi Kutatokozpont, Institute of Organic Chemistry, 2 Magyar tudósok körútja, 1117, Budapest, HUNGARY.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Dec 12, pp. e202404501. Date of Electronic Publication: 2024 Dec 12.
DOI: 10.1002/chem.202404501
Abstrakt: 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.
(© 2024 Wiley‐VCH GmbH.)
Databáze: MEDLINE
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