Studies toward the Caged Sesquiterpenoid Daphnepapytone A

Kamar Shakeri; Letizia Lanfredi; Christian Zachau; Luisa Eichner; Iulia Bîlici; Esra Dural; Jan-H. Dickoff; Manuela Weber; Mathias Christmann

doi:10.1021/acs.joc.6c00079

Studies toward the Caged Sesquiterpenoid Daphnepapytone A

The Journal of Organic Chemistry 2026 Open access

Read full text

Authors: Kamar Shakeri, Letizia Lanfredi, Christian Zachau, Luisa Eichner, Iulia Bîlici, Esra Dural, Jan-H. Dickoff, Manuela Weber, Mathias Christmann

DOI: 10.1021/acs.joc.6c00079

Cited by: 0

References: 46

Abstract

Daphnepapytone A is an unprecedented caged guaiane sesquiterpenoid with α-glucosidase inhibitory activity. We describe progress toward its total synthesis using an α-santonin-type rearrangement strategy. In the course of these studies, a range of guaiane frameworks, including daphbolides A and B, were prepared. However, attempted C9 oxidations of the guaiane proved problematic. Notably, some decalin substrates underwent unexpected rearrangements to yield phenolic products, revealing novel reactivity patterns in this compound class.

Fields of Study & Subjects

Sesquiterpenes and Asteraceae Studies Natural Compound Pharmacology Studies Bioactive Natural Diterpenoids Research

Publication details

Journal / source: The Journal of Organic Chemistry
Publisher: American Chemical Society (ACS)
Volume: 91
Issue: 21
Pages: 7164–7172
Publication date: 15 May 2026
Language: EN

References 46