Work

Biomimetic Synthesis of Cucurbalsaminone A

Year: 2025

Type: article

Abstract: Cucurbalsaminones, notable for their unique 5/6/3/6/5-fused pentacyclic triterpenoid structure, are potent inhibitors of P-glycoprotein. In this study, we propose a biosynthetic pathway starting from lanosterol, aiming to elucidate how these types of complex structures are synthesized by nature. Based on that, we present the first synthesis of cucurbalsaminone A in biomimetic fashion. This synthesis emphasizes key steps including oxidative olefin transposition, Lewis acid-mediated sequential migration of Me and H, and the oxa-di-π-methane rearrangement. This work provides valuable insights into synthesis of complex triterpenoid structures which have potential biological applications.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c00440

Authors: Dattatraya H. Dethe, Chirantan Singha, Salman A. Siddiqui

Institution: Indian Institute of Technology Kanpur

Language: English

Topic: Natural product bioactivities and synthesis

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: green

Funders: Indian Institute of Technology Kanpur, Council of Scientific and Industrial Research, India

Award: G8665703881