Total Syntheses of the Cyclobutane-Containing Guaiane-Type Sesquiterpene Daphnepapytone A and Certain Congeners

Organic Letters 2026

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Authors: Shu Xiao, Ping Lan, Srinivas Beduru, Andrei G. Kutateladze, Xinran Liang, Martin G. Banwell
DOI: 10.1021/acs.orglett.6c00745
Cited by: 2
References: 39

Abstract

Daphnepapytone A ( 1 ), a structurally unique guaiane-type sesquiterpenoid, has been prepared by total synthesis. So, a ( S )-carvone-derived decalindienone was subjected to a photosantonin rearrangement to afford, after additional steps, the natural product oleodaphnone ( 9 ). An intramolecular [2 + 2]-cycloaddition of compound 9 followed by an allylic oxidation then gave target 1 . Four other structures assigned to guaianes were prepared by related means and so identifying two errors in the recent literature.

Fields of Study & Subjects

Sesquiterpenes and Asteraceae Studies Plant chemical constituents analysis Plant biochemistry and biosynthesis

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
15
Pages
4754–4758
Publication date
2 April 2026
Language
EN