Abstract
A simple route to the sesquiterpene antibiotic pentalenolactone 3 has been established. Thus, spiroannulation of 4,4-dimethyl cyclohexanone with bis -(2-iodoethyl)ether, followed by diazo transfer and Wolff rearrangement, gives acid 6. Homologation to the corresponding β-ketoester, followed by diazo transfer and Rh-mediated intramolecular C-H insertion, then gives ester 8. Reduction of 8 followed by dehydration leads to the α,β unsaturated ester, which on exposure to CrO 3 in acetic acid is oxidized preferentially at the less hindered methylene. α-Methylenation then completes the synthesis of 1.
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