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Photocycloadditions of 2-(trimethylsilyloxy)-1,3-butadiene to 2-cycloalkenones. Access to the basic pentalenolactone skeleton

✍ Scribed by Martin Demuth; Bipin Pandey; Bernhard Wietfeld; Hadi Said; José Viader

Publisher
John Wiley and Sons
Year
1988
Tongue
German
Weight
472 KB
Volume
71
Category
Article
ISSN
0018-019X

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✦ Synopsis

The (2 + 21 photocycloaddition of 2-(trimethylsilyloxy)-1,3-butadiene to a number of 2-cycloalkenones proved to be quite a general reaction leading to good yields of the cycloadducts (Table ). This finding is surprising since dienes, in general, are better known as quenchers of enone triplets rather than as photochemical reactants. Both the high substrate concentrations, which can be employed in these cycloadditions, and the remarkable regioand stereoselectivity of the processes qualify them as valuable for syntheses. In a first application, the photoproducts la, b were transformed in three steps into a viable precursor 4 of the pentaleno1actone-G and -H antibiotics. ') Preliminary communication: [I]. ' ) For a summary of related studies in the field of dienone photochemistry, see [3]. ' )

For excellent surveys on polyquinane chemistry, see [14].

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