Work

Stereodivergent Synthesis of 6,12-Guaianolide C1 Epimers via a Rationally Designed Oxy-Cope/Ene Reaction Cascade

Year: 2024

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide Nature synthesizes epimeric C1 guaianolide congeners, key components of major natural product classes, through a single structurally flexible macrocyclic germacranolide core. Our rationally designed elemanolide-type scaffold ( 5 ) now mimics this natural process, enabling the stereodivergent synthesis of both C1 epimers of 6,12-guaianolide lactone motifs. An oxy-Cope/ene cascade acts as the key step of this process, generating two distinct conformers of an intermediate germacranolide, each leading to a specific C1 epimer. Highly stereoselective redox manipulations follow, culminating in the efficient syntheses of diverse osmitopsin-type guaianolides.

Source: Organic Letters

DOI: 10.1021/acs.orglett.4c03504

Authors: Kalliopi Mazaraki, Christos Zangelidis, Antonis Kelesidis, Alexandros L. Zografos

Institutions: Aristotle University of Thessaloniki, Laboratory of Organic Chemistry

Language: English

Topic: Sesquiterpenes and Asteraceae Studies

Subfield: Cancer Research

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Hellenic Academic Libraries Link, General Secretariat for Research and Technology, European Regional Development Fund