Work

Concise synthesis of (±)-gomadalactone A

Year: 2025

Type: article

Abstract: We report the synthesis of (±)-gomadalactone A, a contact sex pheromone of the white-spotted longicorn beetle ( Anoplophora malasiaca ). The synthesis employs Vassilikogiannakis' one-pot, photo-driven cyclopentenone synthesis from a furan derivative, followed by lactonization, to efficiently construct a distinctive 3-oxabicyclo[3.3.0]octane framework. This eleven-step process starts from methyl 2-furylacetate, produced (±)-gomadalactone A in an overall yield of 1 %. • Synthesis of (±)-gomadalactone A. • Employs Vassilikogiannakis' one-pot, photo-driven cyclopentenone synthesis. • Efficient construction of unique 3-oxabicyclo[3.3.0]octane structure achieved. • Required synthetic steps were significantly reduced. • Diastereomeric bicyclic lactone with potential for synthesis of gomadalactone B.

Source: Tetrahedron Letters

DOI: 10.1016/j.tetlet.2025.155623

Authors: Ryosuke Ashizaki, Ryo Katsuta, Shinnosuke Wakamori, Tomoo Nukada, Ken Ishigami

Institution: Tokyo University of Agriculture

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $3,610

OpenAlex ID: W4409920943

FWCI: 0.298

Cites: 22

Cited by: 1

Related to: 10