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May 27, 2026European Journal of Organic Chemistry1 citationsOpen Access

A Short Total Synthesis of the Daucane Sesquiterpenoid Ferutinin

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COChristiane OsthaarYWYuzhou WangAJAnne Jäger

Key Points

  • The aim is to develop a straightforward total synthesis of the sesquiterpenoid ferutinin.
  • Utilized a one-pot sequential conjugate addition/aldol reaction for cyclopentanone formation.
  • Employed ring-closing metathesis to create the hydroazulene core.
  • Completed the synthesis with esterification of the diol to yield ferutinin.
  • Achieved synthesis in only nine steps with an overall yield of 22%.
  • Successfully constructed the daucane skeleton leading to the related compound jaeschkeanadiol.
  • Key transformations were efficient in producing the target compound.

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.

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Cite This Study

Osthaar et al. (2026) studied this question.

synapsesocial.com/papers/6a168ae40c924ddd1bd59b2chttps://doi.org/10.1002/ejoc.70568
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