PubMed · 13663680
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1959-04-09. [Nitrofurans].. https://pubmed.ncbi.nlm.nih.gov/13663680/
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Fluoropropargyl chloride reacted with carbonyl compounds to give propargylic fluorohydrins under mild conditions and in good yields; however, at higher temperatures and longer reaction times, 2,5-disubstituted furans are obtained, also in good yields. Fluorohydrins can be readily oxidized to alpha-fluoroketones and alpha-fluorocarboxylic acids with Jones' reagent.
[reaction: see text] The natural product pachastrissamine, an anhydrophytosphingosine derivative isolated from various sponges and endowed with cytotoxic activity against several human carcinoma cell lines, was synthesized in three steps and with 72% overall yield from d-ribo-phytosphingosine.
[reaction: see text] Starting from 4,4-dimethyl-2-cyclohexenone, an efficient total synthesis of ricciocarpin A (1) in natural form has been accomplished.