Journal
NATURAL PRODUCT RESEARCH
Volume -, Issue -, Pages -Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1080/14786419.2022.2135000
Keywords
Arachnid harvestmen; hydroxy-gamma-lactone; natural product; total synthesis
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Funding
- Education Department, Government of Gujarat [201901420008, 201901420005]
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In this study, we described a novel synthetic strategy for the total synthesis of the harvestmen natural product (4S,5S)-4-hydroxy-gamma-decalactone (minor) using an inexpensive precursor. The synthesis achieved an overall yield of 31% and utilized classical reactions and key steps involving olefin and lactone formation.
Herein, we described the novel synthetic strategy for the total synthesis of harvestmen natural product (4S,5S)-4-hydroxy-gamma-decalactone (minor) from an inexpensive precursor ((R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde) with 31% overall yield. Hydroxyy-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.
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