A Short Total Synthesis of the Daucane Sesquiterpenoid Ferutinin
Abstract
A straightforward total synthesis of the bioactive daucane sesquiterpene ester ferutinin is reported. Starting from 3‐methyl‐2‐cyclopentenone and allyl p ‐tolyl sulfoxide, only nine steps were required to access the target sesquiterpenoid in 22% overall yield. A one‐pot sequential conjugate addition/aldol reaction to set up a trisubstituted cyclopentanone moiety and a ring‐closing metathesis to generate the hydroazulene core were used as the key transformations. Addition of isopropyllithium completed the daucane skeleton and eventually led to the sesquiterpene jaeschkeanadiol. Finally, esterification of this diol gave rise to ferutinin.
Fields of Study & Subjects
Sesquiterpenes and Asteraceae Studies
Traditional and Medicinal Uses of Annonaceae
Marine Sponges and Natural Products
Publication details
- Journal / source
- European Journal of Organic Chemistry
- Publisher
- Wiley
- Volume
- 29
- Issue
- 24
- Publication date
- 25 May 2026
- Language
- EN