A1 Journal article (refereed)
Humilisin E : Strategy for the Synthesis and Access to the Functionalized Bicyclic Core (2024)

Verma, P., Pallerla, R., Rolig, A., & Pihko, P. (2024). Humilisin E : Strategy for the Synthesis and Access to the Functionalized Bicyclic Core. Journal of Organic Chemistry, Early online. https://doi.org/10.1021/acs.joc.4c00358

JYU authors or editors

Publication details

All authors or editors: Verma, Prachi; Pallerla, Rajanish, R.; Rolig, Aino; Pihko, Petri, M.

Journal or series: Journal of Organic Chemistry

ISSN: 0022-3263

eISSN: 1520-6904

Publication year: 2024

Publication date: 26/04/2024

Volume: Early online

Publisher: American Chemical Society (ACS)

Publication country: United States

Publication language: English

DOI: https://doi.org/10.1021/acs.joc.4c00358

Publication open access: Openly available

Publication channel open access: Partially open access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/94670

Web address of parallel published publication (pre-print): https://doi.org/10.26434/chemrxiv-2023-b3173

Abstract

Humilisin E is a diterpenoid possessing a rare epoxidized cyclononene trans-fused with a bicyclo[3.2.0]heptane core. We have identified the P atropisomer of the corresponding cyclononadiene as a potential biosynthetic/synthetic precursor to humilisin E and reported two different strategies for the stereocontrolled synthesis of the appropriately functionalized bicyclic cores of humilisin E. The first route involves a Stork epoxynitrile cyclization via a Mg alkoxide, and the second, more stereoselective approach utilizes the Wolff rearrangement as the key step.

Keywords: organic compounds; chemical synthesis

Contributing organizations

Related projects

Ministry reporting: Yes

Reporting Year: 2024

Preliminary JUFO rating: 2