Bacterial Carotenoids. XXIII. The Carotenoids of Thiorhodaceae. 6. Total Synthesis of Okenone and Related Compounds.

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Abstract
The s tructures of okenone (XIX) and its derivatives okenol (XVIII), okenol acetate (XVI), and anhydro-okenol (XVII) have been confirmed by total synthesis. Renieral (XI), obtained by a Wittig reaction of crocetindial (X) and the ylid IX, was condensed with the ylid XIV to 4''-desoxookenone (XV). Treatment of XV with N-bromo-succinimide and acetic acid gave okenol acetate (XVI) and anhydro-okenol (XVII). The acetate (XVI) was saponified to okenol (XVIII) which was oxidized to okenone (XIX). Effects of the aryl-polyen-one system of okenone (XIX) and renieral (XI) in the electronic, infrared, and proton magnetic resonance spectra are discussed.