Stereoselective total synthesis of arachnid harvestmen natural product: (4S,5S)‑4-hydroxy-γ-decalactone

Abstract

Herein, we described the novel synthetic strategy for the total synthesis of harvestmen natural product (4S,5S)‑4-hydroxy-γ-decalactone (minor) from an inexpensive precursor ((R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde) with 31% overall yield. Hydroxy-γ-lactones represent a special class of harvestmen exocrine defense compounds. The present convergent synthesis utilizes classical reactions like the Barbier reaction, the Grignard reaction, and the employment of an olefin as a masked carboxylic acid functionality followed by lactone formation as key steps.

Graphical Abstract

Keywords:

• Arachnid harvestmen
• hydroxy-γ-lactone
• natural product
• total synthesis

Acknowledgments

M. G. and H. N. Would like to thanks Dr. Gyanchander Eppa for his scientific discussion and guidance, also gratefully acknowledge the Education Department, Government of Gujarat, for Scheme of Developing High-Quality Research (SHODH)-2020 fellowship (ref. nos. 201901420008 and 201901420005). Respectively, all authors thank Indrashil University, Rajpur, Mehsana, Gujarat, India, for providing the infrastructure facility..

Disclosure statement

The authors declare no potential conflict of interest.

Additional information

Funding

M. G. and H. N. gratefully acknowledge the Education Department, Government of Gujarat, for Scheme of Developing High-Quality Research (SHODH)-2020 fellowship (ref nos. 201901420008 and 201901420005).